# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_120515_zb_2401 _database_code_depnum_ccdc_archive 'CCDC 915060' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 O7, C16 H26 N O2, F6 P ' _chemical_formula_sum 'C34 H54 F6 N O9 P' _chemical_formula_weight 765.75 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 22.3036(6) _cell_length_b 15.0552(5) _cell_length_c 31.5788(9) _cell_angle_alpha 90.00 _cell_angle_beta 132.268(2) _cell_angle_gamma 90.00 _cell_volume 7846.8(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7020 _cell_measurement_theta_min 2.8035 _cell_measurement_theta_max 29.4372 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3248 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9362 _exptl_absorpt_correction_T_max 0.9499 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32763 _diffrn_reflns_av_R_equivalents 0.0246 _diffrn_reflns_av_sigmaI/netI 0.0316 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.35 _reflns_number_total 14325 _reflns_number_gt 8849 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1643P)^2^+5.9812P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14325 _refine_ls_number_parameters 925 _refine_ls_number_restraints 85 _refine_ls_R_factor_all 0.1306 _refine_ls_R_factor_gt 0.0896 _refine_ls_wR_factor_ref 0.3046 _refine_ls_wR_factor_gt 0.2622 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 P1 P 0.67301(9) 0.71314(10) 0.93154(6) 0.0754(4) Uani 1 1 d . . . P2 P 0.81912(8) 0.75291(10) 0.75412(6) 0.0751(4) Uani 1 1 d . . . F1 F 0.6382(3) 0.7577(3) 0.87383(19) 0.1445(16) Uani 1 1 d . . . F2 F 0.6113(5) 0.6407(5) 0.8989(4) 0.274(5) Uani 1 1 d . . . F3 F 0.7303(5) 0.6584(5) 0.9326(3) 0.226(4) Uani 1 1 d . . . F4 F 0.7357(5) 0.7851(6) 0.9646(3) 0.254(4) Uani 1 1 d . . . F5 F 0.6133(5) 0.7658(5) 0.9294(4) 0.239(4) Uani 1 1 d . . . F6 F 0.7043(3) 0.6660(4) 0.98790(19) 0.1461(17) Uani 1 1 d . . . F7 F 0.8184(3) 0.7125(5) 0.7087(2) 0.171(2) Uani 1 1 d . . . F8 F 0.7244(2) 0.7618(4) 0.70797(17) 0.1395(16) Uani 1 1 d . . . F9 F 0.8210(3) 0.7996(5) 0.79800(19) 0.216(3) Uani 1 1 d . . . F10 F 0.9107(3) 0.7458(6) 0.7990(2) 0.243(4) Uani 1 1 d . . . F11 F 0.8214(5) 0.8450(4) 0.7327(4) 0.226(3) Uani 1 1 d . . . F12 F 0.8127(7) 0.6651(4) 0.7694(5) 0.311(5) Uani 1 1 d . . . O1 O 0.50293(17) 0.8281(2) 0.49767(12) 0.0616(7) Uani 1 1 d . . . O2 O 0.58680(16) 0.6541(2) 0.54854(12) 0.0598(7) Uani 1 1 d . . . O3 O 0.5578(2) 0.5236(2) 0.60509(14) 0.0700(8) Uani 1 1 d . . . O4 O 0.42639(19) 0.51510(19) 0.60194(13) 0.0664(8) Uani 1 1 d . . . O5 O 0.33006(18) 0.6593(2) 0.58610(13) 0.0680(8) Uani 1 1 d . . . O6 O 0.32277(19) 0.8255(2) 0.53829(14) 0.0696(8) Uani 1 1 d . . . O7 O 0.39076(18) 0.8995(2) 0.49279(13) 0.0650(8) Uani 1 1 d . . . O8 O 0.59040(18) 0.5712(2) 0.78063(14) 0.0736(9) Uani 1 1 d . . . O9 O 0.6738(2) 0.4594(3) 0.8357(2) 0.1103(15) Uani 1 1 d . . . O10 O 1.00512(18) 0.30897(19) 1.02099(12) 0.0644(8) Uani 1 1 d . . . O11 O 1.06683(18) 0.1336(2) 1.02099(14) 0.0676(8) Uani 1 1 d . . . O12 O 1.01943(19) 0.0452(2) 0.91880(14) 0.0696(8) Uani 1 1 d . . . O13 O 0.88401(19) 0.0808(2) 0.80095(14) 0.0740(9) Uani 1 1 d . . . O14 O 0.8155(2) 0.2542(3) 0.75180(16) 0.0900(11) Uani 1 1 d . . . O15 O 0.8345(2) 0.4014(2) 0.81686(16) 0.0862(11) Uani 1 1 d . . . O16 O 0.91600(17) 0.4251(2) 0.93887(14) 0.0690(8) Uani 1 1 d . . . O17 O 1.0310(4) 0.4192(3) 0.7982(3) 0.141(2) Uani 1 1 d . . . O18 O 1.1100(5) 0.5348(4) 0.8288(3) 0.153(2) Uani 1 1 d . . . N1 N 0.43368(18) 0.6931(2) 0.56120(13) 0.0485(7) Uani 1 1 d . . . H1A H 0.3944 0.7239 0.5557 0.058 Uiso 1 1 calc R . . H1B H 0.4412 0.6422 0.5792 0.058 Uiso 1 1 calc R . . N2 N 0.9193(2) 0.2284(2) 0.87438(15) 0.0600(9) Uani 1 1 d . . . H2A H 0.9212 0.1774 0.8605 0.072 Uiso 1 1 calc R . . H2B H 0.8855 0.2654 0.8446 0.072 Uiso 1 1 calc R . . C1 C 0.4535(3) 0.8895(3) 0.45541(18) 0.0619(11) Uani 1 1 d . . . C2 C 0.4588(4) 0.9148(4) 0.4157(2) 0.0836(15) Uani 1 1 d . . . H2 H 0.4965 0.8877 0.4160 0.100 Uiso 1 1 calc R . . C3 C 0.4084(5) 0.9803(5) 0.3758(3) 0.105(2) Uani 1 1 d . . . H3 H 0.4134 0.9978 0.3501 0.126 Uiso 1 1 calc R . . C4 C 0.3518(5) 1.0190(4) 0.3738(2) 0.103(2) Uani 1 1 d . . . H4 H 0.3186 1.0632 0.3470 0.123 Uiso 1 1 calc R . . C5 C 0.3430(3) 0.9928(4) 0.4120(2) 0.0859(15) Uani 1 1 d . . . H5 H 0.3030 1.0182 0.4098 0.103 Uiso 1 1 calc R . . C6 C 0.3943(3) 0.9288(3) 0.45291(18) 0.0630(11) Uani 1 1 d . . . C7 C 0.3362(3) 0.9454(3) 0.4944(2) 0.0747(13) Uani 1 1 d . . . H7A H 0.2807 0.9340 0.4594 0.090 Uiso 1 1 calc R . . H7B H 0.3458 1.0089 0.4971 0.090 Uiso 1 1 calc R . . C8 C 0.3482(3) 0.9150(3) 0.5445(2) 0.0764(13) Uani 1 1 d . . . H8A H 0.4050 0.9201 0.5788 0.092 Uiso 1 1 calc R . . H8B H 0.3177 0.9532 0.5489 0.092 Uiso 1 1 calc R . . C9 C 0.2861(3) 0.8088(4) 0.5606(2) 0.0808(15) Uani 1 1 d . . . H9A H 0.2393 0.8470 0.5419 0.097 Uiso 1 1 calc R . . H9B H 0.3243 0.8217 0.6013 0.097 Uiso 1 1 calc R . . C10 C 0.2608(3) 0.7146(4) 0.5510(2) 0.0809(15) Uani 1 1 d . . . H10A H 0.2273 0.7055 0.5600 0.097 Uiso 1 1 calc R . . H10B H 0.2290 0.6994 0.5111 0.097 Uiso 1 1 calc R . . C11 C 0.3106(3) 0.5692(4) 0.5840(2) 0.0776(14) Uani 1 1 d . . . H11A H 0.2770 0.5473 0.5451 0.093 Uiso 1 1 calc R . . H11B H 0.2803 0.5636 0.5958 0.093 Uiso 1 1 calc R . . C12 C 0.3861(3) 0.5157(4) 0.6226(2) 0.0795(14) Uani 1 1 d . . . H12A H 0.4216 0.5406 0.6608 0.095 Uiso 1 1 calc R . . H12B H 0.3730 0.4553 0.6246 0.095 Uiso 1 1 calc R . . C13 C 0.4924(3) 0.4543(3) 0.6326(2) 0.0742(13) Uani 1 1 d . . . H13A H 0.4750 0.3974 0.6354 0.089 Uiso 1 1 calc R . . H13B H 0.5358 0.4764 0.6710 0.089 Uiso 1 1 calc R . . C14 C 0.5227(3) 0.4429(3) 0.6028(2) 0.0769(14) Uani 1 1 d . . . H14A H 0.5629 0.3959 0.6211 0.092 Uiso 1 1 calc R . . H14B H 0.4783 0.4263 0.5632 0.092 Uiso 1 1 calc R . . C15 C 0.6041(3) 0.5124(3) 0.5895(2) 0.0719(13) Uani 1 1 d . . . H15A H 0.5691 0.4922 0.5502 0.086 Uiso 1 1 calc R . . H15B H 0.6453 0.4675 0.6138 0.086 Uiso 1 1 calc R . . C16 C 0.6432(3) 0.5974(3) 0.5958(2) 0.0692(12) Uani 1 1 d . . . H16A H 0.6644 0.6267 0.6309 0.083 Uiso 1 1 calc R . . H16B H 0.6882 0.5854 0.5982 0.083 Uiso 1 1 calc R . . C17 C 0.6221(3) 0.7372(3) 0.5540(2) 0.0687(12) Uani 1 1 d . . . H17A H 0.6714 0.7268 0.5615 0.082 Uiso 1 1 calc R . . H17B H 0.6363 0.7696 0.5862 0.082 Uiso 1 1 calc R . . C18 C 0.5664(3) 0.7908(3) 0.5021(2) 0.0711(12) Uani 1 1 d . . . H18A H 0.5962 0.8383 0.5026 0.085 Uiso 1 1 calc R . . H18B H 0.5426 0.7540 0.4688 0.085 Uiso 1 1 calc R . . C19 C 0.2990(2) 0.5543(3) 0.46283(17) 0.0530(9) Uani 1 1 d . . . H19 H 0.3394 0.5142 0.4895 0.064 Uiso 1 1 calc R . . C20 C 0.2182(3) 0.5265(3) 0.42389(19) 0.0611(10) Uani 1 1 d . . . C21 C 0.1599(3) 0.5866(3) 0.3844(2) 0.0684(12) Uani 1 1 d . . . H21 H 0.1060 0.5684 0.3583 0.082 Uiso 1 1 calc R . . C22 C 0.1782(3) 0.6733(3) 0.3818(2) 0.0725(12) Uani 1 1 d . . . C23 C 0.2591(3) 0.6989(3) 0.42142(19) 0.0638(11) Uani 1 1 d . . . H23 H 0.2728 0.7567 0.4205 0.077 Uiso 1 1 calc R . . C24 C 0.3198(2) 0.6406(3) 0.46220(16) 0.0492(9) Uani 1 1 d . . . C25 C 0.1964(4) 0.4317(4) 0.4253(3) 0.0916(17) Uani 1 1 d . . . H25A H 0.2440 0.4013 0.4577 0.137 Uiso 1 1 calc R . . H25B H 0.1750 0.4017 0.3908 0.137 Uiso 1 1 calc R . . H25C H 0.1564 0.4323 0.4284 0.137 Uiso 1 1 calc R . . C26 C 0.1128(4) 0.7368(5) 0.3371(3) 0.128(3) Uani 1 1 d . . . H26A H 0.0639 0.7241 0.3292 0.192 Uiso 1 1 calc R . . H26B H 0.1032 0.7301 0.3027 0.192 Uiso 1 1 calc R . . H26C H 0.1296 0.7966 0.3509 0.192 Uiso 1 1 calc R . . C27 C 0.4059(2) 0.6711(3) 0.50430(17) 0.0570(10) Uani 1 1 d . . . H27A H 0.4403 0.6248 0.5091 0.068 Uiso 1 1 calc R . . H27B H 0.4117 0.7232 0.4892 0.068 Uiso 1 1 calc R . . C28 C 0.5097(2) 0.7455(3) 0.59863(16) 0.0490(9) Uani 1 1 d . . . H28A H 0.5011 0.8014 0.5799 0.059 Uiso 1 1 calc R . . H28B H 0.5517 0.7133 0.6034 0.059 Uiso 1 1 calc R . . C29 C 0.5388(3) 0.7644(3) 0.65691(17) 0.0549(9) Uani 1 1 d . . . H29A H 0.4944 0.7892 0.6520 0.066 Uiso 1 1 calc R . . H29B H 0.5814 0.8088 0.6759 0.066 Uiso 1 1 calc R . . C30 C 0.5713(3) 0.6815(3) 0.69546(18) 0.0617(11) Uani 1 1 d . . . H30A H 0.5259 0.6447 0.6825 0.074 Uiso 1 1 calc R . . H30B H 0.6042 0.6471 0.6915 0.074 Uiso 1 1 calc R . . C31 C 0.6216(3) 0.7039(3) 0.75793(18) 0.0670(11) Uani 1 1 d . . . H31A H 0.6651 0.7436 0.7705 0.080 Uiso 1 1 calc R . . H31B H 0.5879 0.7344 0.7625 0.080 Uiso 1 1 calc R . . C32 C 0.6568(3) 0.6219(3) 0.7946(2) 0.0725(13) Uani 1 1 d . . . H32A H 0.6854 0.5869 0.7871 0.087 Uiso 1 1 calc R . . H32B H 0.6948 0.6381 0.8348 0.087 Uiso 1 1 calc R . . C33 C 0.6080(3) 0.4935(4) 0.8058(2) 0.0747(13) Uani 1 1 d . . . C34 C 0.5373(3) 0.4522(5) 0.7931(3) 0.107(2) Uani 1 1 d . . . H34A H 0.4972 0.4377 0.7531 0.160 Uiso 1 1 calc R . . H34B H 0.5147 0.4929 0.8025 0.160 Uiso 1 1 calc R . . H34C H 0.5541 0.3990 0.8154 0.160 Uiso 1 1 calc R . . C35 C 0.9118(2) 0.4272(3) 0.9800(2) 0.0646(12) Uani 1 1 d . . . C36 C 0.8655(3) 0.4886(4) 0.9813(3) 0.0859(16) Uani 1 1 d . . . H36 H 0.8360 0.5320 0.9531 0.103 Uiso 1 1 calc R . . C37 C 0.8635(4) 0.4849(5) 1.0234(3) 0.102(2) Uani 1 1 d . . . H37 H 0.8323 0.5254 1.0238 0.122 Uiso 1 1 calc R . . C38 C 0.9066(4) 0.4228(5) 1.0643(3) 0.104(2) Uani 1 1 d . . . H38 H 0.9049 0.4212 1.0929 0.125 Uiso 1 1 calc R . . C39 C 0.9545(3) 0.3600(4) 1.0655(2) 0.0874(16) Uani 1 1 d . . . H39 H 0.9831 0.3167 1.0939 0.105 Uiso 1 1 calc R . . C40 C 0.9577(2) 0.3645(3) 1.0232(2) 0.0658(12) Uani 1 1 d . . . C41 C 1.0587(3) 0.2513(3) 1.0681(2) 0.0765(13) Uani 1 1 d . . . H41A H 1.0279 0.2086 1.0699 0.092 Uiso 1 1 calc R . . H41B H 1.0922 0.2853 1.1034 0.092 Uiso 1 1 calc R . . C42 C 1.1109(3) 0.2039(3) 1.0619(2) 0.0798(14) Uani 1 1 d . . . H42A H 1.1299 0.2454 1.0496 0.096 Uiso 1 1 calc R . . H42B H 1.1578 0.1796 1.0986 0.096 Uiso 1 1 calc R . . C43 C 1.1171(3) 0.0806(3) 1.0184(2) 0.0749(13) Uani 1 1 d . . . H43A H 1.1602 0.0542 1.0555 0.090 Uiso 1 1 calc R . . H43B H 1.1417 0.1175 1.0084 0.090 Uiso 1 1 calc R . . C44 C 1.0682(3) 0.0093(3) 0.9748(2) 0.0768(13) Uani 1 1 d . . . H44A H 1.1039 -0.0358 0.9803 0.092 Uiso 1 1 calc R . . H44B H 1.0338 -0.0187 0.9796 0.092 Uiso 1 1 calc R . . C45 C 0.9768(3) -0.0217(3) 0.8760(2) 0.0786(14) Uani 1 1 d . . . H45A H 0.9328 -0.0443 0.8724 0.094 Uiso 1 1 calc R . . H45B H 1.0130 -0.0707 0.8868 0.094 Uiso 1 1 calc R . . C46 C 0.9435(3) 0.0157(3) 0.8198(2) 0.0761(13) Uani 1 1 d . . . H46A H 0.9869 0.0423 0.8240 0.091 Uiso 1 1 calc R . . H46B H 0.9195 -0.0314 0.7916 0.091 Uiso 1 1 calc R . . C47 C 0.8381(4) 0.1044(5) 0.7422(2) 0.0928(17) Uani 1 1 d . . . H47A H 0.8120 0.0519 0.7184 0.111 Uiso 1 1 calc R . . H47B H 0.8742 0.1279 0.7379 0.111 Uiso 1 1 calc R . . C48 C 0.7764(4) 0.1713(5) 0.7236(2) 0.0985(19) Uani 1 1 d . . . H48A H 0.7397 0.1791 0.6824 0.118 Uiso 1 1 calc R . . H48B H 0.7451 0.1515 0.7329 0.118 Uiso 1 1 calc R . . C49 C 0.7634(4) 0.3274(6) 0.7291(3) 0.115(2) Uani 1 1 d . . . H49A H 0.7214 0.3160 0.7300 0.138 Uiso 1 1 calc R . . H49B H 0.7375 0.3358 0.6896 0.138 Uiso 1 1 calc R . . C50 C 0.8074(5) 0.4083(5) 0.7616(3) 0.119(2) Uani 1 1 d . . . H50A H 0.8534 0.4163 0.7648 0.143 Uiso 1 1 calc R . . H50B H 0.7722 0.4595 0.7419 0.143 Uiso 1 1 calc R . . C51 C 0.8778(3) 0.4786(4) 0.8520(3) 0.0925(19) Uani 1 1 d . . . H51A H 0.8574 0.5309 0.8279 0.111 Uiso 1 1 calc R . . H51B H 0.9348 0.4723 0.8723 0.111 Uiso 1 1 calc R . . C52 C 0.8680(3) 0.4899(3) 0.8939(2) 0.0800(15) Uani 1 1 d . . . H52A H 0.8849 0.5492 0.9101 0.096 Uiso 1 1 calc R . . H52B H 0.8114 0.4829 0.8746 0.096 Uiso 1 1 calc R . . C53 C 0.7881(2) 0.0812(3) 0.84576(17) 0.0553(10) Uani 1 1 d . . . H53 H 0.8325 0.0431 0.8683 0.066 Uiso 1 1 calc R . . C54 C 0.7114(3) 0.0459(3) 0.80284(19) 0.0606(10) Uani 1 1 d . . . C55 C 0.6469(3) 0.1048(3) 0.7706(2) 0.0733(13) Uani 1 1 d . . . H55 H 0.5951 0.0824 0.7413 0.088 Uiso 1 1 calc R . . C56 C 0.6561(3) 0.1948(3) 0.7802(3) 0.0824(15) Uani 1 1 d . . . C57 C 0.7340(3) 0.2269(3) 0.8234(2) 0.0687(12) Uani 1 1 d . . . H57 H 0.7418 0.2876 0.8309 0.082 Uiso 1 1 calc R . . C58 C 0.8000(2) 0.1713(3) 0.85560(16) 0.0515(9) Uani 1 1 d . . . C59 C 0.6989(4) -0.0525(3) 0.7916(3) 0.0950(17) Uani 1 1 d . . . H59A H 0.7146 -0.0698 0.7710 0.143 Uiso 1 1 calc R . . H59B H 0.6428 -0.0665 0.7692 0.143 Uiso 1 1 calc R . . H59C H 0.7313 -0.0839 0.8273 0.143 Uiso 1 1 calc R . . C60 C 0.5835(4) 0.2559(5) 0.7433(4) 0.159(4) Uani 1 1 d . . . H60A H 0.5468 0.2347 0.7045 0.239 Uiso 1 1 calc R . . H60B H 0.6012 0.3148 0.7444 0.239 Uiso 1 1 calc R . . H60C H 0.5566 0.2572 0.7574 0.239 Uiso 1 1 calc R . . C61 C 0.8844(2) 0.2091(3) 0.90000(17) 0.0614(11) Uani 1 1 d . . . H61A H 0.8825 0.2633 0.9157 0.074 Uiso 1 1 calc R . . H61B H 0.9187 0.1670 0.9311 0.074 Uiso 1 1 calc R . . C62 C 1.0007(3) 0.2681(4) 0.9129(3) 0.0861(15) Uani 1 1 d DU . . H62A H 1.0390 0.2300 0.9457 0.103 Uiso 1 1 calc R . . H62B H 1.0002 0.3258 0.9263 0.103 Uiso 1 1 calc R . . C63 C 1.0242(5) 0.2774(7) 0.8745(5) 0.174(3) Uani 1 1 d DU . . H63A H 1.0158 0.2203 0.8569 0.208 Uiso 1 1 calc R . . H63B H 0.9873 0.3194 0.8439 0.208 Uiso 1 1 calc R . . C64 C 1.1037(6) 0.3051(8) 0.9041(5) 0.200(3) Uani 1 1 d DU . . H64A H 1.1426 0.2674 0.9370 0.240 Uiso 1 1 calc R . . H64B H 1.1119 0.3661 0.9168 0.240 Uiso 1 1 calc R . . C65 C 1.1115(6) 0.2958(7) 0.8583(4) 0.147(2) Uani 1 1 d DU . . H65A H 1.1629 0.2679 0.8759 0.176 Uiso 1 1 calc R . . H65B H 1.0686 0.2576 0.8275 0.176 Uiso 1 1 calc R . . C66 C 1.1073(6) 0.3710(7) 0.8377(5) 0.160(2) Uani 1 1 d DU . . H66A H 1.1272 0.3624 0.8185 0.192 Uiso 1 1 calc R . . H66B H 1.1454 0.4101 0.8699 0.192 Uiso 1 1 calc R . . C67 C 1.0418(6) 0.5037(5) 0.7989(4) 0.1141(19) Uani 1 1 d U . . C68 C 0.9706(6) 0.5559(5) 0.7653(4) 0.134(2) Uani 1 1 d U . . H68A H 0.9253 0.5200 0.7355 0.201 Uiso 1 1 calc R . . H68B H 0.9766 0.6044 0.7487 0.201 Uiso 1 1 calc R . . H68C H 0.9616 0.5788 0.7890 0.201 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 P1 0.0827(9) 0.0720(9) 0.0856(9) 0.0009(7) 0.0624(8) 0.0044(7) P2 0.0679(7) 0.0799(9) 0.0624(7) 0.0037(6) 0.0377(6) 0.0109(7) F1 0.178(4) 0.162(4) 0.123(3) 0.044(3) 0.113(3) 0.042(3) F2 0.230(7) 0.189(7) 0.216(7) -0.001(6) 0.074(6) -0.101(6) F3 0.267(7) 0.290(8) 0.204(6) 0.109(6) 0.192(6) 0.185(7) F4 0.294(9) 0.253(8) 0.197(6) -0.094(6) 0.158(6) -0.179(7) F5 0.326(8) 0.258(7) 0.333(9) 0.176(7) 0.302(8) 0.190(7) F6 0.160(4) 0.181(4) 0.131(3) 0.057(3) 0.111(3) 0.039(3) F7 0.127(3) 0.268(7) 0.122(3) -0.049(4) 0.086(3) 0.000(4) F8 0.081(2) 0.204(5) 0.104(3) -0.006(3) 0.050(2) 0.005(3) F9 0.175(5) 0.335(9) 0.094(3) -0.029(4) 0.072(3) 0.102(5) F10 0.073(2) 0.431(11) 0.128(4) -0.072(5) 0.028(3) 0.055(4) F11 0.230(7) 0.159(5) 0.246(7) 0.028(5) 0.142(6) -0.044(5) F12 0.439(14) 0.129(5) 0.465(15) 0.151(7) 0.345(13) 0.061(7) O1 0.0657(16) 0.0663(18) 0.0649(17) 0.0084(15) 0.0489(15) 0.0020(15) O2 0.0555(15) 0.0657(19) 0.0618(17) -0.0055(15) 0.0408(14) -0.0013(14) O3 0.089(2) 0.0487(17) 0.081(2) -0.0077(15) 0.0607(19) 0.0026(16) O4 0.0801(19) 0.0551(18) 0.0672(18) 0.0044(15) 0.0508(17) -0.0067(16) O5 0.0642(17) 0.076(2) 0.0736(19) -0.0025(17) 0.0503(16) -0.0096(16) O6 0.0798(19) 0.064(2) 0.090(2) -0.0047(17) 0.0673(19) 0.0060(16) O7 0.0676(17) 0.0564(18) 0.0683(18) 0.0085(15) 0.0446(16) 0.0097(14) O8 0.0660(18) 0.079(2) 0.077(2) 0.0291(18) 0.0487(17) 0.0172(16) O9 0.067(2) 0.088(3) 0.151(4) 0.043(3) 0.063(2) 0.020(2) O10 0.0663(17) 0.0541(17) 0.0559(16) 0.0032(14) 0.0343(15) 0.0047(14) O11 0.0654(17) 0.0549(18) 0.077(2) 0.0015(16) 0.0458(17) 0.0033(15) O12 0.080(2) 0.0516(18) 0.084(2) -0.0046(16) 0.0584(19) -0.0032(15) O13 0.0739(19) 0.088(2) 0.072(2) -0.0112(18) 0.0534(18) -0.0053(18) O14 0.075(2) 0.108(3) 0.074(2) 0.023(2) 0.045(2) 0.014(2) O15 0.077(2) 0.081(2) 0.086(2) 0.034(2) 0.049(2) 0.0057(19) O16 0.0553(16) 0.0559(18) 0.088(2) 0.0156(16) 0.0450(17) 0.0086(14) O17 0.195(5) 0.068(3) 0.238(7) 0.022(3) 0.178(6) 0.017(3) O18 0.187(6) 0.133(5) 0.223(7) 0.011(4) 0.173(6) 0.004(4) N1 0.0526(17) 0.0473(18) 0.0515(18) -0.0036(14) 0.0375(16) -0.0023(14) N2 0.061(2) 0.064(2) 0.061(2) 0.0045(17) 0.0436(18) -0.0012(17) C1 0.068(3) 0.054(3) 0.055(2) -0.002(2) 0.038(2) -0.015(2) C2 0.104(4) 0.085(4) 0.067(3) 0.000(3) 0.060(3) -0.020(3) C3 0.126(5) 0.106(5) 0.066(3) 0.012(3) 0.058(4) -0.025(4) C4 0.118(5) 0.077(4) 0.066(3) 0.018(3) 0.043(4) -0.004(4) C5 0.087(3) 0.064(3) 0.069(3) 0.006(3) 0.037(3) 0.004(3) C6 0.069(3) 0.046(2) 0.050(2) -0.0011(19) 0.030(2) -0.011(2) C7 0.074(3) 0.053(3) 0.089(3) -0.002(2) 0.052(3) 0.008(2) C8 0.076(3) 0.066(3) 0.087(3) -0.011(3) 0.055(3) 0.007(2) C9 0.083(3) 0.092(4) 0.094(4) 0.009(3) 0.071(3) 0.024(3) C10 0.063(3) 0.110(4) 0.087(3) 0.008(3) 0.058(3) 0.003(3) C11 0.085(3) 0.087(4) 0.085(3) -0.011(3) 0.068(3) -0.026(3) C12 0.105(4) 0.070(3) 0.085(3) 0.004(3) 0.072(3) -0.018(3) C13 0.092(3) 0.042(2) 0.075(3) 0.010(2) 0.051(3) 0.001(2) C14 0.083(3) 0.039(2) 0.078(3) 0.000(2) 0.041(3) 0.006(2) C15 0.076(3) 0.059(3) 0.068(3) 0.000(2) 0.043(2) 0.021(2) C16 0.052(2) 0.080(3) 0.062(3) -0.003(2) 0.033(2) 0.013(2) C17 0.061(2) 0.077(3) 0.083(3) -0.007(3) 0.055(3) -0.004(2) C18 0.081(3) 0.072(3) 0.087(3) -0.003(3) 0.067(3) -0.009(3) C19 0.051(2) 0.054(2) 0.055(2) -0.0013(19) 0.0360(19) 0.0008(18) C20 0.065(2) 0.056(3) 0.069(3) -0.007(2) 0.048(2) -0.008(2) C21 0.050(2) 0.075(3) 0.067(3) -0.008(2) 0.034(2) -0.008(2) C22 0.059(3) 0.071(3) 0.067(3) 0.005(2) 0.034(2) 0.007(2) C23 0.071(3) 0.049(2) 0.064(3) 0.000(2) 0.042(2) -0.003(2) C24 0.055(2) 0.051(2) 0.048(2) -0.0096(18) 0.0380(19) -0.0066(18) C25 0.088(3) 0.069(3) 0.117(5) 0.001(3) 0.068(4) -0.017(3) C26 0.082(4) 0.108(5) 0.115(5) 0.025(4) 0.034(4) 0.019(4) C27 0.061(2) 0.068(3) 0.056(2) -0.015(2) 0.045(2) -0.014(2) C28 0.052(2) 0.045(2) 0.053(2) -0.0037(17) 0.0364(19) -0.0058(17) C29 0.064(2) 0.048(2) 0.053(2) -0.0050(18) 0.040(2) -0.0012(19) C30 0.071(3) 0.056(3) 0.058(2) -0.004(2) 0.043(2) -0.007(2) C31 0.078(3) 0.064(3) 0.057(3) 0.001(2) 0.045(2) -0.001(2) C32 0.067(3) 0.081(3) 0.060(3) 0.009(2) 0.039(2) -0.001(2) C33 0.067(3) 0.079(3) 0.081(3) 0.019(3) 0.050(3) 0.012(3) C34 0.080(3) 0.119(5) 0.128(5) 0.051(4) 0.073(4) 0.017(3) C35 0.048(2) 0.052(3) 0.078(3) -0.013(2) 0.036(2) -0.011(2) C36 0.056(3) 0.066(3) 0.113(4) -0.019(3) 0.048(3) -0.007(2) C37 0.071(3) 0.108(5) 0.113(5) -0.051(4) 0.057(4) -0.014(3) C38 0.087(4) 0.134(6) 0.091(4) -0.051(4) 0.059(4) -0.018(4) C39 0.082(3) 0.101(4) 0.065(3) -0.026(3) 0.044(3) -0.015(3) C40 0.051(2) 0.063(3) 0.064(3) -0.022(2) 0.030(2) -0.015(2) C41 0.084(3) 0.062(3) 0.055(3) 0.002(2) 0.035(3) 0.007(3) C42 0.065(3) 0.065(3) 0.061(3) 0.009(2) 0.023(2) 0.014(2) C43 0.066(3) 0.072(3) 0.080(3) 0.018(3) 0.046(3) 0.020(2) C44 0.090(3) 0.060(3) 0.099(4) 0.016(3) 0.071(3) 0.019(3) C45 0.088(3) 0.060(3) 0.108(4) -0.009(3) 0.074(3) -0.004(3) C46 0.085(3) 0.066(3) 0.097(4) -0.019(3) 0.069(3) -0.005(3) C47 0.093(4) 0.120(5) 0.073(3) -0.011(3) 0.059(3) -0.001(4) C48 0.080(3) 0.135(6) 0.058(3) -0.006(3) 0.037(3) -0.005(4) C49 0.106(5) 0.135(6) 0.071(4) 0.036(4) 0.046(4) 0.031(5) C50 0.128(5) 0.113(6) 0.116(5) 0.064(5) 0.083(5) 0.042(5) C51 0.071(3) 0.069(3) 0.120(5) 0.044(3) 0.057(3) 0.009(3) C52 0.058(2) 0.050(3) 0.110(4) 0.022(3) 0.048(3) 0.006(2) C53 0.051(2) 0.058(3) 0.059(2) 0.008(2) 0.038(2) 0.0059(19) C54 0.066(3) 0.054(2) 0.070(3) -0.006(2) 0.050(2) -0.007(2) C55 0.050(2) 0.072(3) 0.080(3) -0.010(3) 0.036(2) -0.011(2) C56 0.053(2) 0.063(3) 0.106(4) 0.000(3) 0.043(3) 0.006(2) C57 0.061(3) 0.056(3) 0.085(3) -0.007(2) 0.047(3) -0.003(2) C58 0.051(2) 0.056(2) 0.052(2) -0.0019(19) 0.0362(19) -0.0045(18) C59 0.096(4) 0.056(3) 0.115(4) -0.010(3) 0.064(4) -0.007(3) C60 0.063(3) 0.088(5) 0.201(9) 0.006(5) 0.037(5) 0.018(3) C61 0.051(2) 0.079(3) 0.050(2) -0.002(2) 0.032(2) -0.010(2) C62 0.073(3) 0.091(3) 0.126(4) 0.020(3) 0.080(3) -0.001(3) C63 0.124(4) 0.166(5) 0.219(5) 0.035(5) 0.110(4) -0.004(4) C64 0.166(4) 0.179(5) 0.207(5) 0.019(4) 0.106(4) 0.007(4) C65 0.164(4) 0.171(5) 0.193(5) 0.043(4) 0.156(4) 0.024(4) C66 0.162(4) 0.153(5) 0.218(5) 0.030(4) 0.150(4) 0.020(4) C67 0.169(5) 0.106(5) 0.164(5) 0.015(4) 0.152(4) 0.013(4) C68 0.164(6) 0.112(5) 0.157(6) 0.015(5) 0.120(6) 0.019(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 P1 F2 1.496(6) . ? P1 F4 1.501(6) . ? P1 F3 1.501(5) . ? P1 F5 1.513(5) . ? P1 F1 1.572(4) . ? P1 F6 1.577(4) . ? P2 F12 1.447(5) . ? P2 F10 1.515(4) . ? P2 F9 1.530(4) . ? P2 F7 1.550(4) . ? P2 F11 1.558(6) . ? P2 F8 1.569(4) . ? O1 C1 1.368(5) . ? O1 C18 1.439(5) . ? O2 C16 1.418(5) . ? O2 C17 1.426(5) . ? O3 C14 1.420(6) . ? O3 C15 1.420(6) . ? O4 C12 1.419(5) . ? O4 C13 1.423(6) . ? O5 C11 1.413(6) . ? O5 C10 1.416(6) . ? O6 C9 1.415(6) . ? O6 C8 1.424(6) . ? O7 C6 1.386(5) . ? O7 C7 1.431(5) . ? O8 C33 1.317(6) . ? O8 C32 1.446(6) . ? O9 C33 1.203(6) . ? O10 C40 1.386(5) . ? O10 C41 1.415(5) . ? O11 C43 1.424(5) . ? O11 C42 1.430(6) . ? O12 C44 1.421(6) . ? O12 C45 1.421(6) . ? O13 C46 1.418(6) . ? O13 C47 1.435(6) . ? O14 C49 1.400(8) . ? O14 C48 1.437(8) . ? O15 C50 1.414(8) . ? O15 C51 1.440(7) . ? O16 C35 1.365(6) . ? O16 C52 1.439(6) . ? O17 C67 1.292(8) . ? O17 C66 1.457(10) . ? O18 C67 1.221(10) . ? N1 C28 1.483(5) . ? N1 C27 1.492(5) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C62 1.469(6) . ? N2 C61 1.480(5) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? C1 C2 1.389(6) . ? C1 C6 1.400(7) . ? C2 C3 1.386(9) . ? C2 H2 0.9300 . ? C3 C4 1.351(10) . ? C3 H3 0.9300 . ? C4 C5 1.404(9) . ? C4 H4 0.9300 . ? C5 C6 1.386(7) . ? C5 H5 0.9300 . ? C7 C8 1.488(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.480(8) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.487(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.490(7) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.486(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.463(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C24 1.385(6) . ? C19 C20 1.399(6) . ? C19 H19 0.9300 . ? C20 C21 1.372(6) . ? C20 C25 1.517(6) . ? C21 C22 1.386(7) . ? C21 H21 0.9300 . ? C22 C23 1.390(6) . ? C22 C26 1.505(8) . ? C23 C24 1.383(6) . ? C23 H23 0.9300 . ? C24 C27 1.494(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.511(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 C30 1.543(6) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 C31 1.512(6) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.503(6) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.476(7) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C40 1.385(7) . ? C35 C36 1.406(7) . ? C36 C37 1.362(9) . ? C36 H36 0.9300 . ? C37 C38 1.341(10) . ? C37 H37 0.9300 . ? C38 C39 1.408(9) . ? C38 H38 0.9300 . ? C39 C40 1.389(7) . ? C39 H39 0.9300 . ? C41 C42 1.487(7) . ? C41 H41A 0.9700 . ? C41 H41B 0.9700 . ? C42 H42A 0.9700 . ? C42 H42B 0.9700 . ? C43 C44 1.489(7) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 H44A 0.9700 . ? C44 H44B 0.9700 . ? C45 C46 1.498(7) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9700 . ? C46 H46B 0.9700 . ? C47 C48 1.471(8) . ? C47 H47A 0.9700 . ? C47 H47B 0.9700 . ? C48 H48A 0.9700 . ? C48 H48B 0.9700 . ? C49 C50 1.465(11) . ? C49 H49A 0.9700 . ? C49 H49B 0.9700 . ? C50 H50A 0.9700 . ? C50 H50B 0.9700 . ? C51 C52 1.488(8) . ? C51 H51A 0.9700 . ? C51 H51B 0.9700 . ? C52 H52A 0.9700 . ? C52 H52B 0.9700 . ? C53 C58 1.378(6) . ? C53 C54 1.388(6) . ? C53 H53 0.9300 . ? C54 C55 1.387(6) . ? C54 C59 1.505(7) . ? C55 C56 1.373(7) . ? C55 H55 0.9300 . ? C56 C57 1.388(7) . ? C56 C60 1.512(7) . ? C57 C58 1.374(6) . ? C57 H57 0.9300 . ? C58 C61 1.511(5) . ? C59 H59A 0.9600 . ? C59 H59B 0.9600 . ? C59 H59C 0.9600 . ? C60 H60A 0.9600 . ? C60 H60B 0.9600 . ? C60 H60C 0.9600 . ? C61 H61A 0.9700 . ? C61 H61B 0.9700 . ? C62 C63 1.619(10) . ? C62 H62A 0.9700 . ? C62 H62B 0.9700 . ? C63 C64 1.402(8) . ? C63 H63A 0.9700 . ? C63 H63B 0.9700 . ? C64 C65 1.575(12) . ? C64 H64A 0.9700 . ? C64 H64B 0.9700 . ? C65 C66 1.277(10) . ? C65 H65A 0.9700 . ? C65 H65B 0.9700 . ? C66 H66A 0.9700 . ? C66 H66B 0.9700 . ? C67 C68 1.414(11) . ? C68 H68A 0.9600 . ? C68 H68B 0.9600 . ? C68 H68C 0.9600 . ? 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 F2 P1 F4 179.4(6) . . ? F2 P1 F3 89.5(6) . . ? F4 P1 F3 90.0(5) . . ? F2 P1 F5 88.6(6) . . ? F4 P1 F5 91.9(6) . . ? F3 P1 F5 178.1(6) . . ? F2 P1 F1 90.3(4) . . ? F4 P1 F1 90.0(4) . . ? F3 P1 F1 90.6(3) . . ? F5 P1 F1 89.5(3) . . ? F2 P1 F6 87.3(4) . . ? F4 P1 F6 92.4(4) . . ? F3 P1 F6 90.2(3) . . ? F5 P1 F6 89.6(3) . . ? F1 P1 F6 177.4(3) . . ? F12 P2 F10 89.9(6) . . ? F12 P2 F9 93.8(6) . . ? F10 P2 F9 89.3(3) . . ? F12 P2 F7 90.6(5) . . ? F10 P2 F7 90.3(3) . . ? F9 P2 F7 175.7(4) . . ? F12 P2 F11 175.6(6) . . ? F10 P2 F11 93.0(5) . . ? F9 P2 F11 89.7(5) . . ? F7 P2 F11 86.0(4) . . ? F12 P2 F8 90.8(5) . . ? F10 P2 F8 179.1(4) . . ? F9 P2 F8 90.1(3) . . ? F7 P2 F8 90.3(3) . . ? F11 P2 F8 86.4(4) . . ? C1 O1 C18 116.9(3) . . ? C16 O2 C17 112.0(3) . . ? C14 O3 C15 112.6(3) . . ? C12 O4 C13 112.1(4) . . ? C11 O5 C10 112.9(4) . . ? C9 O6 C8 114.2(4) . . ? C6 O7 C7 116.6(4) . . ? C33 O8 C32 117.1(4) . . ? C40 O10 C41 116.8(4) . . ? C43 O11 C42 112.2(4) . . ? C44 O12 C45 112.2(4) . . ? C46 O13 C47 111.5(4) . . ? C49 O14 C48 114.7(5) . . ? C50 O15 C51 113.5(5) . . ? C35 O16 C52 116.3(4) . . ? C67 O17 C66 112.3(8) . . ? C28 N1 C27 113.8(3) . . ? C28 N1 H1A 108.8 . . ? C27 N1 H1A 108.8 . . ? C28 N1 H1B 108.8 . . ? C27 N1 H1B 108.8 . . ? H1A N1 H1B 107.7 . . ? C62 N2 C61 116.0(4) . . ? C62 N2 H2A 108.3 . . ? C61 N2 H2A 108.3 . . ? C62 N2 H2B 108.3 . . ? C61 N2 H2B 108.3 . . ? H2A N2 H2B 107.4 . . ? O1 C1 C2 124.3(5) . . ? O1 C1 C6 116.8(4) . . ? C2 C1 C6 118.9(5) . . ? C3 C2 C1 120.4(6) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C4 C3 C2 120.7(6) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.3(6) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 119.5(6) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 O7 123.5(5) . . ? C5 C6 C1 120.2(5) . . ? O7 C6 C1 116.3(4) . . ? O7 C7 C8 109.9(4) . . ? O7 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? O7 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O6 C8 C7 112.0(4) . . ? O6 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? O6 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? O6 C9 C10 109.7(4) . . ? O6 C9 H9A 109.7 . . ? C10 C9 H9A 109.7 . . ? O6 C9 H9B 109.7 . . ? C10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? O5 C10 C9 109.8(4) . . ? O5 C10 H10A 109.7 . . ? C9 C10 H10A 109.7 . . ? O5 C10 H10B 109.7 . . ? C9 C10 H10B 109.7 . . ? H10A C10 H10B 108.2 . . ? O5 C11 C12 109.8(4) . . ? O5 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? O5 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O4 C12 C11 110.2(4) . . ? O4 C12 H12A 109.6 . . ? C11 C12 H12A 109.6 . . ? O4 C12 H12B 109.6 . . ? C11 C12 H12B 109.6 . . ? H12A C12 H12B 108.1 . . ? O4 C13 C14 110.3(4) . . ? O4 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? O4 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? O3 C14 C13 109.7(4) . . ? O3 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? O3 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? O3 C15 C16 110.5(4) . . ? O3 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O3 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? O2 C16 C15 110.6(4) . . ? O2 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? O2 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? O2 C17 C18 111.4(4) . . ? O2 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? O2 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? O1 C18 C17 111.3(4) . . ? O1 C18 H18A 109.4 . . ? C17 C18 H18A 109.4 . . ? O1 C18 H18B 109.4 . . ? C17 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C24 C19 C20 120.9(4) . . ? C24 C19 H19 119.5 . . ? C20 C19 H19 119.5 . . ? C21 C20 C19 118.3(4) . . ? C21 C20 C25 121.4(4) . . ? C19 C20 C25 120.3(4) . . ? C20 C21 C22 122.5(4) . . ? C20 C21 H21 118.7 . . ? C22 C21 H21 118.7 . . ? C21 C22 C23 117.6(4) . . ? C21 C22 C26 121.0(5) . . ? C23 C22 C26 121.4(5) . . ? C24 C23 C22 121.8(4) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C23 C24 C19 118.7(4) . . ? C23 C24 C27 120.1(4) . . ? C19 C24 C27 121.2(4) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N1 C27 C24 112.6(3) . . ? N1 C27 H27A 109.1 . . ? C24 C27 H27A 109.1 . . ? N1 C27 H27B 109.1 . . ? C24 C27 H27B 109.1 . . ? H27A C27 H27B 107.8 . . ? N1 C28 C29 113.3(3) . . ? N1 C28 H28A 108.9 . . ? C29 C28 H28A 108.9 . . ? N1 C28 H28B 108.9 . . ? C29 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C28 C29 C30 113.4(3) . . ? C28 C29 H29A 108.9 . . ? C30 C29 H29A 108.9 . . ? C28 C29 H29B 108.9 . . ? C30 C29 H29B 108.9 . . ? H29A C29 H29B 107.7 . . ? C31 C30 C29 113.1(4) . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30B 109.0 . . ? C29 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C32 C31 C30 111.6(4) . . ? C32 C31 H31A 109.3 . . ? C30 C31 H31A 109.3 . . ? C32 C31 H31B 109.3 . . ? C30 C31 H31B 109.3 . . ? H31A C31 H31B 108.0 . . ? O8 C32 C31 107.4(4) . . ? O8 C32 H32A 110.2 . . ? C31 C32 H32A 110.2 . . ? O8 C32 H32B 110.2 . . ? C31 C32 H32B 110.2 . . ? H32A C32 H32B 108.5 . . ? O9 C33 O8 124.3(5) . . ? O9 C33 C34 123.3(5) . . ? O8 C33 C34 112.4(4) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O16 C35 C40 116.2(4) . . ? O16 C35 C36 124.3(5) . . ? C40 C35 C36 119.4(5) . . ? C37 C36 C35 120.5(6) . . ? C37 C36 H36 119.7 . . ? C35 C36 H36 119.7 . . ? C38 C37 C36 119.7(6) . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C37 C38 C39 122.3(6) . . ? C37 C38 H38 118.8 . . ? C39 C38 H38 118.8 . . ? C40 C39 C38 118.0(6) . . ? C40 C39 H39 121.0 . . ? C38 C39 H39 121.0 . . ? C35 C40 O10 116.5(4) . . ? C35 C40 C39 119.9(5) . . ? O10 C40 C39 123.6(5) . . ? O10 C41 C42 109.8(4) . . ? O10 C41 H41A 109.7 . . ? C42 C41 H41A 109.7 . . ? O10 C41 H41B 109.7 . . ? C42 C41 H41B 109.7 . . ? H41A C41 H41B 108.2 . . ? O11 C42 C41 110.5(4) . . ? O11 C42 H42A 109.5 . . ? C41 C42 H42A 109.5 . . ? O11 C42 H42B 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 108.1 . . ? O11 C43 C44 109.9(4) . . ? O11 C43 H43A 109.7 . . ? C44 C43 H43A 109.7 . . ? O11 C43 H43B 109.7 . . ? C44 C43 H43B 109.7 . . ? H43A C43 H43B 108.2 . . ? O12 C44 C43 110.3(4) . . ? O12 C44 H44A 109.6 . . ? C43 C44 H44A 109.6 . . ? O12 C44 H44B 109.6 . . ? C43 C44 H44B 109.6 . . ? H44A C44 H44B 108.1 . . ? O12 C45 C46 110.0(4) . . ? O12 C45 H45A 109.7 . . ? C46 C45 H45A 109.7 . . ? O12 C45 H45B 109.7 . . ? C46 C45 H45B 109.7 . . ? H45A C45 H45B 108.2 . . ? O13 C46 C45 109.6(4) . . ? O13 C46 H46A 109.7 . . ? C45 C46 H46A 109.7 . . ? O13 C46 H46B 109.7 . . ? C45 C46 H46B 109.7 . . ? H46A C46 H46B 108.2 . . ? O13 C47 C48 110.4(4) . . ? O13 C47 H47A 109.6 . . ? C48 C47 H47A 109.6 . . ? O13 C47 H47B 109.6 . . ? C48 C47 H47B 109.6 . . ? H47A C47 H47B 108.1 . . ? O14 C48 C47 109.4(5) . . ? O14 C48 H48A 109.8 . . ? C47 C48 H48A 109.8 . . ? O14 C48 H48B 109.8 . . ? C47 C48 H48B 109.8 . . ? H48A C48 H48B 108.2 . . ? O14 C49 C50 111.2(6) . . ? O14 C49 H49A 109.4 . . ? C50 C49 H49A 109.4 . . ? O14 C49 H49B 109.4 . . ? C50 C49 H49B 109.4 . . ? H49A C49 H49B 108.0 . . ? O15 C50 C49 109.4(5) . . ? O15 C50 H50A 109.8 . . ? C49 C50 H50A 109.8 . . ? O15 C50 H50B 109.8 . . ? C49 C50 H50B 109.8 . . ? H50A C50 H50B 108.2 . . ? O15 C51 C52 110.7(4) . . ? O15 C51 H51A 109.5 . . ? C52 C51 H51A 109.5 . . ? O15 C51 H51B 109.5 . . ? C52 C51 H51B 109.5 . . ? H51A C51 H51B 108.1 . . ? O16 C52 C51 110.1(4) . . ? O16 C52 H52A 109.6 . . ? C51 C52 H52A 109.6 . . ? O16 C52 H52B 109.6 . . ? C51 C52 H52B 109.6 . . ? H52A C52 H52B 108.2 . . ? C58 C53 C54 121.3(4) . . ? C58 C53 H53 119.3 . . ? C54 C53 H53 119.3 . . ? C55 C54 C53 117.5(4) . . ? C55 C54 C59 121.3(4) . . ? C53 C54 C59 121.2(4) . . ? C56 C55 C54 122.8(4) . . ? C56 C55 H55 118.6 . . ? C54 C55 H55 118.6 . . ? C55 C56 C57 117.6(4) . . ? C55 C56 C60 120.4(5) . . ? C57 C56 C60 121.9(5) . . ? C58 C57 C56 121.7(4) . . ? C58 C57 H57 119.2 . . ? C56 C57 H57 119.2 . . ? C57 C58 C53 119.1(4) . . ? C57 C58 C61 120.2(4) . . ? C53 C58 C61 120.7(4) . . ? C54 C59 H59A 109.5 . . ? C54 C59 H59B 109.5 . . ? H59A C59 H59B 109.5 . . ? C54 C59 H59C 109.5 . . ? H59A C59 H59C 109.5 . . ? H59B C59 H59C 109.5 . . ? C56 C60 H60A 109.5 . . ? C56 C60 H60B 109.5 . . ? H60A C60 H60B 109.5 . . ? C56 C60 H60C 109.5 . . ? H60A C60 H60C 109.5 . . ? H60B C60 H60C 109.5 . . ? N2 C61 C58 110.6(3) . . ? N2 C61 H61A 109.5 . . ? C58 C61 H61A 109.5 . . ? N2 C61 H61B 109.5 . . ? C58 C61 H61B 109.5 . . ? H61A C61 H61B 108.1 . . ? N2 C62 C63 104.9(5) . . ? N2 C62 H62A 110.8 . . ? C63 C62 H62A 110.8 . . ? N2 C62 H62B 110.8 . . ? C63 C62 H62B 110.8 . . ? H62A C62 H62B 108.8 . . ? C64 C63 C62 115.4(9) . . ? C64 C63 H63A 108.4 . . ? C62 C63 H63A 108.4 . . ? C64 C63 H63B 108.4 . . ? C62 C63 H63B 108.4 . . ? H63A C63 H63B 107.5 . . ? C63 C64 C65 103.5(9) . . ? C63 C64 H64A 111.1 . . ? C65 C64 H64A 111.1 . . ? C63 C64 H64B 111.1 . . ? C65 C64 H64B 111.1 . . ? H64A C64 H64B 109.0 . . ? C66 C65 C64 111.9(10) . . ? C66 C65 H65A 109.2 . . ? C64 C65 H65A 109.2 . . ? C66 C65 H65B 109.2 . . ? C64 C65 H65B 109.2 . . ? H65A C65 H65B 107.9 . . ? C65 C66 O17 121.5(9) . . ? C65 C66 H66A 106.9 . . ? O17 C66 H66A 106.9 . . ? C65 C66 H66B 106.9 . . ? O17 C66 H66B 106.9 . . ? H66A C66 H66B 106.7 . . ? O18 C67 O17 120.7(8) . . ? O18 C67 C68 123.6(8) . . ? O17 C67 C68 115.6(9) . . ? C67 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C67 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C18 O1 C1 C2 2.7(6) . . . . ? C18 O1 C1 C6 -177.1(4) . . . . ? O1 C1 C2 C3 -177.4(5) . . . . ? C6 C1 C2 C3 2.5(7) . . . . ? C1 C2 C3 C4 -1.7(9) . . . . ? C2 C3 C4 C5 -0.5(10) . . . . ? C3 C4 C5 C6 1.9(9) . . . . ? C4 C5 C6 O7 179.2(5) . . . . ? C4 C5 C6 C1 -1.1(7) . . . . ? C7 O7 C6 C5 -6.5(6) . . . . ? C7 O7 C6 C1 173.8(4) . . . . ? O1 C1 C6 C5 178.8(4) . . . . ? C2 C1 C6 C5 -1.1(7) . . . . ? O1 C1 C6 O7 -1.5(5) . . . . ? C2 C1 C6 O7 178.6(4) . . . . ? C6 O7 C7 C8 -171.9(4) . . . . ? C9 O6 C8 C7 -143.4(4) . . . . ? O7 C7 C8 O6 -68.4(5) . . . . ? C8 O6 C9 C10 179.0(4) . . . . ? C11 O5 C10 C9 173.3(4) . . . . ? O6 C9 C10 O5 69.5(5) . . . . ? C10 O5 C11 C12 -179.1(4) . . . . ? C13 O4 C12 C11 -171.3(4) . . . . ? O5 C11 C12 O4 -66.0(5) . . . . ? C12 O4 C13 C14 169.2(4) . . . . ? C15 O3 C14 C13 166.4(4) . . . . ? O4 C13 C14 O3 66.7(5) . . . . ? C14 O3 C15 C16 -176.8(4) . . . . ? C17 O2 C16 C15 178.5(3) . . . . ? O3 C15 C16 O2 -78.9(5) . . . . ? C16 O2 C17 C18 173.2(4) . . . . ? C1 O1 C18 C17 171.1(4) . . . . ? O2 C17 C18 O1 74.8(5) . . . . ? C24 C19 C20 C21 1.0(6) . . . . ? C24 C19 C20 C25 -179.7(4) . . . . ? C19 C20 C21 C22 -0.2(7) . . . . ? C25 C20 C21 C22 -179.5(5) . . . . ? C20 C21 C22 C23 -0.2(7) . . . . ? C20 C21 C22 C26 178.7(6) . . . . ? C21 C22 C23 C24 -0.1(7) . . . . ? C26 C22 C23 C24 -179.1(5) . . . . ? C22 C23 C24 C19 0.9(6) . . . . ? C22 C23 C24 C27 -179.4(4) . . . . ? C20 C19 C24 C23 -1.4(6) . . . . ? C20 C19 C24 C27 179.0(4) . . . . ? C28 N1 C27 C24 -164.5(3) . . . . ? C23 C24 C27 N1 100.2(4) . . . . ? C19 C24 C27 N1 -80.1(5) . . . . ? C27 N1 C28 C29 -177.9(3) . . . . ? N1 C28 C29 C30 70.6(4) . . . . ? C28 C29 C30 C31 163.5(4) . . . . ? C29 C30 C31 C32 -176.1(4) . . . . ? C33 O8 C32 C31 176.0(4) . . . . ? C30 C31 C32 O8 -67.9(5) . . . . ? C32 O8 C33 O9 -6.3(8) . . . . ? C32 O8 C33 C34 174.0(5) . . . . ? C52 O16 C35 C40 179.7(4) . . . . ? C52 O16 C35 C36 -1.1(6) . . . . ? O16 C35 C36 C37 178.7(5) . . . . ? C40 C35 C36 C37 -2.1(7) . . . . ? C35 C36 C37 C38 0.6(8) . . . . ? C36 C37 C38 C39 -0.2(9) . . . . ? C37 C38 C39 C40 1.3(9) . . . . ? O16 C35 C40 O10 2.4(5) . . . . ? C36 C35 C40 O10 -176.8(4) . . . . ? O16 C35 C40 C39 -177.6(4) . . . . ? C36 C35 C40 C39 3.2(6) . . . . ? C41 O10 C40 C35 173.4(4) . . . . ? C41 O10 C40 C39 -6.7(6) . . . . ? C38 C39 C40 C35 -2.8(7) . . . . ? C38 C39 C40 O10 177.3(4) . . . . ? C40 O10 C41 C42 -173.9(4) . . . . ? C43 O11 C42 C41 -173.6(4) . . . . ? O10 C41 C42 O11 -77.2(5) . . . . ? C42 O11 C43 C44 -179.4(4) . . . . ? C45 O12 C44 C43 175.1(4) . . . . ? O11 C43 C44 O12 74.8(5) . . . . ? C44 O12 C45 C46 -165.9(4) . . . . ? C47 O13 C46 C45 -167.3(4) . . . . ? O12 C45 C46 O13 -65.5(5) . . . . ? C46 O13 C47 C48 179.5(5) . . . . ? C49 O14 C48 C47 167.4(5) . . . . ? O13 C47 C48 O14 69.4(6) . . . . ? C48 O14 C49 C50 177.8(5) . . . . ? C51 O15 C50 C49 -179.3(5) . . . . ? O14 C49 C50 O15 -68.1(7) . . . . ? C50 O15 C51 C52 151.0(5) . . . . ? C35 O16 C52 C51 -179.1(4) . . . . ? O15 C51 C52 O16 74.1(5) . . . . ? C58 C53 C54 C55 -0.7(6) . . . . ? C58 C53 C54 C59 178.9(5) . . . . ? C53 C54 C55 C56 -1.0(7) . . . . ? C59 C54 C55 C56 179.3(6) . . . . ? C54 C55 C56 C57 1.2(9) . . . . ? C54 C55 C56 C60 179.4(7) . . . . ? C55 C56 C57 C58 0.3(8) . . . . ? C60 C56 C57 C58 -177.8(7) . . . . ? C56 C57 C58 C53 -2.0(7) . . . . ? C56 C57 C58 C61 176.4(5) . . . . ? C54 C53 C58 C57 2.2(6) . . . . ? C54 C53 C58 C61 -176.2(4) . . . . ? C62 N2 C61 C58 178.3(4) . . . . ? C57 C58 C61 N2 -89.7(5) . . . . ? C53 C58 C61 N2 88.7(5) . . . . ? C61 N2 C62 C63 177.6(5) . . . . ? N2 C62 C63 C64 -173.3(9) . . . . ? C62 C63 C64 C65 172.9(8) . . . . ? C63 C64 C65 C66 103.4(12) . . . . ? C64 C65 C66 O17 -72.5(14) . . . . ? C67 O17 C66 C65 155.2(10) . . . . ? C66 O17 C67 O18 2.7(10) . . . . ? C66 O17 C67 C68 -174.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.018 _refine_diff_density_min -0.879 _refine_diff_density_rms 0.064 data_120920_zb_266 _database_code_depnum_ccdc_archive 'CCDC 915061' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 O7, C17 H28 N O2, F6 P' _chemical_formula_sum 'C35 H56 F6 N O9 P' _chemical_formula_weight 779.78 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.7822(7) _cell_length_b 15.4270(8) _cell_length_c 19.5317(10) _cell_angle_alpha 90.00 _cell_angle_beta 91.937(5) _cell_angle_gamma 90.00 _cell_volume 3849.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 3918 _cell_measurement_theta_min 3.0788 _cell_measurement_theta_max 29.4965 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1656 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9443 _exptl_absorpt_correction_T_max 0.9528 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15124 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7025 _reflns_number_gt 5069 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0632P)^2^+3.5879P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7025 _refine_ls_number_parameters 477 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.1525 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 P1 P 1.22550(6) 0.40422(5) 0.07834(4) 0.0366(2) Uani 1 1 d . . . F1 F 1.11029(17) 0.39472(16) 0.09847(18) 0.1048(10) Uani 1 1 d . . . F2 F 1.2091(2) 0.50383(14) 0.06452(13) 0.0915(8) Uani 1 1 d . . . F3 F 1.2529(2) 0.4227(2) 0.15659(12) 0.1055(10) Uani 1 1 d . . . F4 F 1.2029(2) 0.38526(16) 0.00066(11) 0.0965(9) Uani 1 1 d . . . F5 F 1.24102(18) 0.30303(14) 0.09152(11) 0.0736(7) Uani 1 1 d . . . F6 F 1.34565(18) 0.4121(2) 0.06273(15) 0.1047(9) Uani 1 1 d . . . O1 O 0.96567(14) 0.67050(11) 0.38978(9) 0.0316(4) Uani 1 1 d . . . O2 O 1.00382(14) 0.63753(12) 0.24500(9) 0.0347(4) Uani 1 1 d . . . O3 O 0.93480(14) 0.49074(12) 0.15738(9) 0.0337(4) Uani 1 1 d . . . O4 O 0.80975(14) 0.34310(12) 0.18252(9) 0.0351(4) Uani 1 1 d . . . O5 O 0.79266(14) 0.28329(11) 0.31982(9) 0.0315(4) Uani 1 1 d . . . O6 O 0.80223(14) 0.38726(11) 0.44569(9) 0.0304(4) Uani 1 1 d . . . O7 O 0.86495(14) 0.56933(11) 0.47289(9) 0.0312(4) Uani 1 1 d . . . O8 O 1.05504(16) 0.16285(14) 0.19490(11) 0.0474(5) Uani 1 1 d . . . O9 O 1.16815(19) 0.08788(17) 0.13310(13) 0.0638(7) Uani 1 1 d . . . N1 N 0.88294(16) 0.45103(13) 0.29565(10) 0.0256(5) Uani 1 1 d . . . H1A H 0.8541 0.3969 0.3012 0.031 Uiso 1 1 calc R . . H1B H 0.8964 0.4576 0.2500 0.031 Uiso 1 1 calc R . . C1 C 0.9113(2) 0.71102(17) 0.44015(13) 0.0296(6) Uani 1 1 d . . . C2 C 0.8539(2) 0.65697(17) 0.48304(13) 0.0296(6) Uani 1 1 d . . . C3 C 0.7919(2) 0.6938(2) 0.53214(14) 0.0385(7) Uani 1 1 d . . . H3 H 0.7507 0.6579 0.5602 0.046 Uiso 1 1 calc R . . C4 C 0.7901(3) 0.7838(2) 0.54026(16) 0.0479(8) Uani 1 1 d . . . H4 H 0.7474 0.8088 0.5739 0.057 Uiso 1 1 calc R . . C5 C 0.8486(3) 0.8360(2) 0.50052(16) 0.0462(8) Uani 1 1 d . . . H5 H 0.8481 0.8970 0.5073 0.055 Uiso 1 1 calc R . . C6 C 0.9093(2) 0.80009(18) 0.45007(15) 0.0389(7) Uani 1 1 d . . . H6 H 0.9497 0.8368 0.4222 0.047 Uiso 1 1 calc R . . C7 C 1.0244(2) 0.72593(18) 0.34602(15) 0.0371(7) Uani 1 1 d . . . H7A H 1.0770 0.7588 0.3739 0.045 Uiso 1 1 calc R . . H7B H 0.9767 0.7680 0.3228 0.045 Uiso 1 1 calc R . . C8 C 1.0782(2) 0.67309(19) 0.29377(15) 0.0370(7) Uani 1 1 d . . . H8A H 1.1287 0.7099 0.2698 0.044 Uiso 1 1 calc R . . H8B H 1.1176 0.6255 0.3168 0.044 Uiso 1 1 calc R . . C9 C 1.0537(2) 0.60726(19) 0.18550(15) 0.0386(7) Uani 1 1 d . . . H9A H 1.1051 0.5617 0.1987 0.046 Uiso 1 1 calc R . . H9B H 1.0921 0.6557 0.1645 0.046 Uiso 1 1 calc R . . C10 C 0.9751(2) 0.57114(19) 0.13421(14) 0.0384(7) Uani 1 1 d . . . H10A H 0.9169 0.6129 0.1271 0.046 Uiso 1 1 calc R . . H10B H 1.0086 0.5625 0.0898 0.046 Uiso 1 1 calc R . . C11 C 0.8812(2) 0.4430(2) 0.10387(14) 0.0388(7) Uani 1 1 d . . . H11A H 0.9199 0.4478 0.0610 0.047 Uiso 1 1 calc R . . H11B H 0.8103 0.4673 0.0955 0.047 Uiso 1 1 calc R . . C12 C 0.8732(2) 0.34968(19) 0.12422(13) 0.0370(7) Uani 1 1 d . . . H12A H 0.8417 0.3156 0.0859 0.044 Uiso 1 1 calc R . . H12B H 0.9438 0.3261 0.1352 0.044 Uiso 1 1 calc R . . C13 C 0.7866(2) 0.25601(17) 0.19947(14) 0.0349(6) Uani 1 1 d . . . H13A H 0.8523 0.2227 0.2066 0.042 Uiso 1 1 calc R . . H13B H 0.7450 0.2286 0.1617 0.042 Uiso 1 1 calc R . . C14 C 0.7259(2) 0.25559(18) 0.26360(15) 0.0352(6) Uani 1 1 d . . . H14A H 0.6651 0.2951 0.2584 0.042 Uiso 1 1 calc R . . H14B H 0.6994 0.1965 0.2724 0.042 Uiso 1 1 calc R . . C15 C 0.7528(2) 0.25928(18) 0.38432(14) 0.0372(7) Uani 1 1 d . . . H15A H 0.7511 0.1953 0.3881 0.045 Uiso 1 1 calc R . . H15B H 0.6803 0.2810 0.3877 0.045 Uiso 1 1 calc R . . C16 C 0.8196(2) 0.29590(17) 0.44169(14) 0.0360(6) Uani 1 1 d . . . H16A H 0.8017 0.2681 0.4854 0.043 Uiso 1 1 calc R . . H16B H 0.8943 0.2843 0.4335 0.043 Uiso 1 1 calc R . . C17 C 0.8457(2) 0.42164(18) 0.50823(13) 0.0332(6) Uani 1 1 d . . . H17A H 0.9230 0.4198 0.5074 0.040 Uiso 1 1 calc R . . H17B H 0.8233 0.3858 0.5472 0.040 Uiso 1 1 calc R . . C18 C 0.8102(2) 0.51312(18) 0.51768(13) 0.0338(6) Uani 1 1 d . . . H18A H 0.7340 0.5173 0.5076 0.041 Uiso 1 1 calc R . . H18B H 0.8239 0.5311 0.5658 0.041 Uiso 1 1 calc R . . C19 C 0.5624(2) 0.5448(2) 0.10721(15) 0.0473(8) Uani 1 1 d . . . H19A H 0.5407 0.6057 0.1082 0.071 Uiso 1 1 calc R . . H19B H 0.5064 0.5099 0.0856 0.071 Uiso 1 1 calc R . . H19C H 0.6261 0.5393 0.0810 0.071 Uiso 1 1 calc R . . C20 C 0.4410(2) 0.3907(2) 0.31759(18) 0.0507(8) Uani 1 1 d . . . H20A H 0.4181 0.4241 0.3570 0.076 Uiso 1 1 calc R . . H20B H 0.4693 0.3348 0.3333 0.076 Uiso 1 1 calc R . . H20C H 0.3813 0.3808 0.2857 0.076 Uiso 1 1 calc R . . C21 C 0.6796(2) 0.52930(16) 0.21308(13) 0.0287(6) Uani 1 1 d . . . H21 H 0.7327 0.5591 0.1897 0.034 Uiso 1 1 calc R . . C22 C 0.5838(2) 0.51334(17) 0.17926(14) 0.0328(6) Uani 1 1 d . . . C23 C 0.5082(2) 0.46829(17) 0.21419(15) 0.0359(7) Uani 1 1 d . . . H23 H 0.4430 0.4560 0.1915 0.043 Uiso 1 1 calc R . . C24 C 0.5253(2) 0.44064(17) 0.28150(15) 0.0349(6) Uani 1 1 d . . . C25 C 0.6213(2) 0.45900(16) 0.31430(14) 0.0303(6) Uani 1 1 d . . . H25 H 0.6336 0.4415 0.3605 0.036 Uiso 1 1 calc R . . C26 C 0.69929(19) 0.50255(15) 0.28043(13) 0.0260(5) Uani 1 1 d . . . C27 C 0.8043(2) 0.51817(16) 0.31532(13) 0.0284(6) Uani 1 1 d . . . H27A H 0.8300 0.5763 0.3026 0.034 Uiso 1 1 calc R . . H27B H 0.7967 0.5171 0.3656 0.034 Uiso 1 1 calc R . . C28 C 0.98417(19) 0.45549(17) 0.33620(13) 0.0282(6) Uani 1 1 d . . . H28A H 0.9744 0.4307 0.3823 0.034 Uiso 1 1 calc R . . H28B H 1.0051 0.5169 0.3420 0.034 Uiso 1 1 calc R . . C29 C 1.0709(2) 0.40626(17) 0.30142(13) 0.0291(6) Uani 1 1 d . . . H29A H 1.0776 0.4297 0.2546 0.035 Uiso 1 1 calc R . . H29B H 1.1377 0.4175 0.3269 0.035 Uiso 1 1 calc R . . C30 C 1.0548(2) 0.30897(17) 0.29648(14) 0.0317(6) Uani 1 1 d . . . H30A H 0.9933 0.2970 0.2657 0.038 Uiso 1 1 calc R . . H30B H 1.0393 0.2861 0.3424 0.038 Uiso 1 1 calc R . . C31 C 1.1497(2) 0.26158(18) 0.26963(15) 0.0337(6) Uani 1 1 d . . . H31A H 1.1724 0.2910 0.2276 0.040 Uiso 1 1 calc R . . H31B H 1.2079 0.2654 0.3043 0.040 Uiso 1 1 calc R . . C32 C 1.1285(2) 0.16746(19) 0.25360(16) 0.0417(7) Uani 1 1 d . . . H32A H 1.1945 0.1377 0.2429 0.050 Uiso 1 1 calc R . . H32B H 1.0983 0.1385 0.2937 0.050 Uiso 1 1 calc R . . C33 C 1.0856(3) 0.1238(2) 0.13823(17) 0.0472(8) Uani 1 1 d . A . C34 C 1.0022(3) 0.1301(3) 0.08239(19) 0.0641(10) Uani 1 1 d D . . H34A H 0.9755 0.0712 0.0721 0.077 Uiso 0.635(6) 1 calc PR A 1 H34B H 0.9433 0.1646 0.0996 0.077 Uiso 0.635(6) 1 calc PR A 1 H34C H 0.9364 0.1059 0.0996 0.077 Uiso 0.365(6) 1 calc PR A 2 H34D H 0.9896 0.1921 0.0719 0.077 Uiso 0.365(6) 1 calc PR A 2 C35 C 1.0360(5) 0.1689(5) 0.0195(3) 0.0714(16) Uani 0.635(6) 1 d PD A 1 H35A H 1.0624 0.2275 0.0289 0.107 Uiso 0.635(6) 1 calc PR A 1 H35B H 0.9768 0.1719 -0.0136 0.107 Uiso 0.635(6) 1 calc PR A 1 H35C H 1.0919 0.1336 0.0006 0.107 Uiso 0.635(6) 1 calc PR A 1 C35A C 1.0265(9) 0.0859(8) 0.0196(5) 0.0714(16) Uani 0.365(6) 1 d PD A 2 H35D H 1.0982 0.0999 0.0073 0.107 Uiso 0.365(6) 1 calc PR A 2 H35E H 0.9776 0.1047 -0.0172 0.107 Uiso 0.365(6) 1 calc PR A 2 H35F H 1.0200 0.0232 0.0262 0.107 Uiso 0.365(6) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0333(4) 0.0414(4) 0.0355(4) 0.0017(3) 0.0078(3) 0.0030(3) F1 0.0452(13) 0.0756(16) 0.197(3) 0.0161(18) 0.0479(16) 0.0094(11) F2 0.138(2) 0.0414(12) 0.0977(19) 0.0080(12) 0.0461(17) 0.0018(13) F3 0.142(3) 0.127(2) 0.0472(14) -0.0090(14) -0.0008(14) -0.0368(19) F4 0.155(3) 0.0836(17) 0.0488(13) -0.0057(12) -0.0313(15) 0.0299(16) F5 0.0919(17) 0.0555(13) 0.0745(15) 0.0136(11) 0.0193(12) 0.0272(11) F6 0.0471(14) 0.147(3) 0.121(2) 0.0222(19) 0.0236(14) -0.0040(14) O1 0.0318(10) 0.0265(9) 0.0365(10) 0.0000(8) 0.0019(8) -0.0036(8) O2 0.0269(10) 0.0426(11) 0.0348(10) 0.0015(9) 0.0056(8) -0.0006(8) O3 0.0373(11) 0.0393(11) 0.0245(9) 0.0044(8) 0.0011(8) 0.0031(8) O4 0.0366(11) 0.0357(11) 0.0327(10) -0.0069(8) -0.0001(8) 0.0015(8) O5 0.0321(10) 0.0301(10) 0.0322(10) -0.0031(8) -0.0018(8) -0.0064(8) O6 0.0373(10) 0.0278(9) 0.0258(9) 0.0019(8) -0.0038(8) -0.0044(8) O7 0.0365(10) 0.0280(10) 0.0295(10) -0.0024(8) 0.0043(8) -0.0038(8) O8 0.0392(12) 0.0518(13) 0.0511(13) -0.0176(11) 0.0009(10) 0.0058(10) O9 0.0560(15) 0.0789(18) 0.0573(15) -0.0098(13) 0.0137(12) 0.0204(13) N1 0.0283(11) 0.0254(11) 0.0227(11) -0.0013(9) -0.0025(9) -0.0009(9) C1 0.0296(14) 0.0296(14) 0.0290(14) -0.0068(12) -0.0088(11) 0.0019(11) C2 0.0303(14) 0.0314(14) 0.0265(13) -0.0044(12) -0.0090(11) 0.0007(11) C3 0.0431(17) 0.0451(17) 0.0269(14) -0.0057(13) -0.0028(12) 0.0055(14) C4 0.060(2) 0.0499(19) 0.0330(16) -0.0128(15) -0.0062(15) 0.0202(16) C5 0.061(2) 0.0345(16) 0.0418(18) -0.0110(14) -0.0142(16) 0.0087(15) C6 0.0450(17) 0.0315(15) 0.0394(16) -0.0028(13) -0.0120(13) -0.0017(13) C7 0.0325(15) 0.0318(15) 0.0467(17) 0.0062(13) -0.0058(13) -0.0105(12) C8 0.0251(14) 0.0414(16) 0.0446(17) 0.0100(14) 0.0007(12) -0.0067(12) C9 0.0353(16) 0.0384(16) 0.0431(17) 0.0074(13) 0.0149(13) 0.0004(13) C10 0.0450(17) 0.0394(16) 0.0313(15) 0.0103(13) 0.0085(13) 0.0108(13) C11 0.0387(16) 0.0552(19) 0.0222(14) 0.0001(13) -0.0040(12) 0.0078(14) C12 0.0372(16) 0.0476(17) 0.0257(14) -0.0081(13) -0.0044(12) 0.0062(13) C13 0.0349(15) 0.0307(14) 0.0384(16) -0.0111(12) -0.0079(12) 0.0001(12) C14 0.0298(15) 0.0296(14) 0.0457(17) -0.0079(13) -0.0066(12) -0.0040(11) C15 0.0460(17) 0.0272(14) 0.0389(16) 0.0009(12) 0.0081(13) -0.0093(12) C16 0.0477(17) 0.0263(14) 0.0341(15) 0.0058(12) 0.0027(13) -0.0018(12) C17 0.0386(16) 0.0363(15) 0.0243(13) 0.0048(12) -0.0029(11) -0.0068(12) C18 0.0359(15) 0.0416(16) 0.0239(13) -0.0025(12) 0.0022(11) -0.0070(12) C19 0.0452(18) 0.0536(19) 0.0420(18) 0.0067(15) -0.0150(14) 0.0009(15) C20 0.0405(18) 0.0486(19) 0.064(2) 0.0053(17) 0.0091(16) -0.0107(15) C21 0.0287(14) 0.0246(13) 0.0327(14) 0.0007(11) 0.0004(11) 0.0006(11) C22 0.0350(15) 0.0289(14) 0.0341(15) -0.0012(12) -0.0057(12) 0.0052(12) C23 0.0268(14) 0.0300(14) 0.0504(18) -0.0040(13) -0.0068(12) 0.0028(11) C24 0.0302(15) 0.0275(14) 0.0473(17) -0.0026(13) 0.0062(13) 0.0007(11) C25 0.0339(15) 0.0259(13) 0.0312(14) 0.0005(11) 0.0024(11) 0.0032(11) C26 0.0258(13) 0.0215(12) 0.0306(14) -0.0026(11) -0.0008(11) 0.0023(10) C27 0.0308(14) 0.0243(13) 0.0297(14) -0.0001(11) -0.0029(11) 0.0019(11) C28 0.0290(14) 0.0286(13) 0.0265(13) 0.0000(11) -0.0065(11) -0.0017(11) C29 0.0257(13) 0.0325(14) 0.0287(14) 0.0009(11) -0.0028(10) -0.0006(11) C30 0.0256(14) 0.0331(14) 0.0366(15) 0.0015(12) 0.0027(11) -0.0001(11) C31 0.0279(14) 0.0362(15) 0.0371(16) 0.0011(12) 0.0021(12) 0.0013(12) C32 0.0357(16) 0.0420(17) 0.0475(18) -0.0024(14) 0.0026(13) 0.0053(13) C33 0.0471(19) 0.0476(19) 0.0477(19) -0.0061(15) 0.0116(15) 0.0007(15) C34 0.056(2) 0.083(3) 0.054(2) -0.016(2) 0.0074(18) 0.0069(19) C35 0.065(3) 0.092(4) 0.057(3) -0.004(3) 0.003(3) -0.009(3) C35A 0.065(3) 0.092(4) 0.057(3) -0.004(3) 0.003(3) -0.009(3) _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 P1 F1 1.544(2) . ? P1 F4 1.563(2) . ? P1 F2 1.573(2) . ? P1 F6 1.581(2) . ? P1 F3 1.582(2) . ? P1 F5 1.593(2) . ? O1 C1 1.374(3) . ? O1 C7 1.439(3) . ? O2 C9 1.423(3) . ? O2 C8 1.432(3) . ? O3 C10 1.423(3) . ? O3 C11 1.434(3) . ? O4 C13 1.417(3) . ? O4 C12 1.423(3) . ? O5 C15 1.424(3) . ? O5 C14 1.433(3) . ? O6 C17 1.427(3) . ? O6 C16 1.429(3) . ? O7 C2 1.374(3) . ? O7 C18 1.431(3) . ? O8 C33 1.331(4) . ? O8 C32 1.459(4) . ? O9 C33 1.199(4) . ? N1 C28 1.496(3) . ? N1 C27 1.502(3) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? C1 C6 1.388(4) . ? C1 C2 1.406(4) . ? C2 C3 1.386(4) . ? C3 C4 1.399(4) . ? C3 H3 0.9500 . ? C4 C5 1.360(5) . ? C4 H4 0.9500 . ? C5 C6 1.390(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.492(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.502(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.497(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.496(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.497(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.495(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C22 1.505(4) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C24 1.517(4) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.392(4) . ? C21 C26 1.394(4) . ? C21 H21 0.9500 . ? C22 C23 1.388(4) . ? C23 C24 1.392(4) . ? C23 H23 0.9500 . ? C24 C25 1.394(4) . ? C25 C26 1.388(4) . ? C25 H25 0.9500 . ? C26 C27 1.504(3) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.522(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.518(4) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.524(4) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.508(4) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.503(5) . ? C34 C35 1.445(7) . ? C34 C35A 1.446(10) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C34 H34C 0.9900 . ? C34 H34D 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C35A H35D 0.9800 . ? C35A H35E 0.9800 . ? C35A H35F 0.9800 . ? 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 F1 P1 F4 94.73(18) . . ? F1 P1 F2 90.78(14) . . ? F4 P1 F2 89.83(14) . . ? F1 P1 F6 176.21(18) . . ? F4 P1 F6 88.65(17) . . ? F2 P1 F6 90.94(16) . . ? F1 P1 F3 87.33(18) . . ? F4 P1 F3 177.84(17) . . ? F2 P1 F3 90.79(16) . . ? F6 P1 F3 89.27(17) . . ? F1 P1 F5 88.88(13) . . ? F4 P1 F5 89.51(13) . . ? F2 P1 F5 179.23(16) . . ? F6 P1 F5 89.44(15) . . ? F3 P1 F5 89.88(15) . . ? C1 O1 C7 116.2(2) . . ? C9 O2 C8 111.3(2) . . ? C10 O3 C11 112.7(2) . . ? C13 O4 C12 112.6(2) . . ? C15 O5 C14 112.2(2) . . ? C17 O6 C16 110.9(2) . . ? C2 O7 C18 116.9(2) . . ? C33 O8 C32 118.5(2) . . ? C28 N1 C27 114.02(19) . . ? C28 N1 H1A 108.7 . . ? C27 N1 H1A 108.7 . . ? C28 N1 H1B 108.7 . . ? C27 N1 H1B 108.7 . . ? H1A N1 H1B 107.6 . . ? O1 C1 C6 124.2(3) . . ? O1 C1 C2 116.3(2) . . ? C6 C1 C2 119.4(3) . . ? O7 C2 C3 124.5(2) . . ? O7 C2 C1 116.0(2) . . ? C3 C2 C1 119.4(2) . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.8(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 120.0(3) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C1 C6 C5 120.5(3) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O1 C7 C8 110.1(2) . . ? O1 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? O1 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 110.7(2) . . ? O2 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C10 111.0(2) . . ? O2 C9 H9A 109.4 . . ? C10 C9 H9A 109.4 . . ? O2 C9 H9B 109.4 . . ? C10 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? O3 C10 C9 110.6(2) . . ? O3 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O3 C11 C12 109.6(2) . . ? O3 C11 H11A 109.7 . . ? C12 C11 H11A 109.7 . . ? O3 C11 H11B 109.7 . . ? C12 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? O4 C12 C11 109.1(2) . . ? O4 C12 H12A 109.9 . . ? C11 C12 H12A 109.9 . . ? O4 C12 H12B 109.9 . . ? C11 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? O4 C13 C14 108.5(2) . . ? O4 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? O4 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? O5 C14 C13 109.1(2) . . ? O5 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? O5 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? O5 C15 C16 110.6(2) . . ? O5 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? O6 C16 C15 109.1(2) . . ? O6 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? O6 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? O6 C17 C18 110.2(2) . . ? O6 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? O6 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? O7 C18 C17 109.9(2) . . ? O7 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? O7 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C22 C19 H19A 109.5 . . ? C22 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C22 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C24 C20 H20A 109.5 . . ? C24 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C24 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C26 121.6(2) . . ? C22 C21 H21 119.2 . . ? C26 C21 H21 119.2 . . ? C23 C22 C21 118.1(3) . . ? C23 C22 C19 120.9(3) . . ? C21 C22 C19 121.1(3) . . ? C22 C23 C24 121.9(3) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C23 C24 C25 118.6(3) . . ? C23 C24 C20 120.2(3) . . ? C25 C24 C20 121.2(3) . . ? C26 C25 C24 121.0(2) . . ? C26 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C25 C26 C21 118.9(2) . . ? C25 C26 C27 120.4(2) . . ? C21 C26 C27 120.7(2) . . ? N1 C27 C26 111.6(2) . . ? N1 C27 H27A 109.3 . . ? C26 C27 H27A 109.3 . . ? N1 C27 H27B 109.3 . . ? C26 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? N1 C28 C29 111.7(2) . . ? N1 C28 H28A 109.3 . . ? C29 C28 H28A 109.3 . . ? N1 C28 H28B 109.3 . . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 107.9 . . ? C30 C29 C28 115.0(2) . . ? C30 C29 H29A 108.5 . . ? C28 C29 H29A 108.5 . . ? C30 C29 H29B 108.5 . . ? C28 C29 H29B 108.5 . . ? H29A C29 H29B 107.5 . . ? C29 C30 C31 112.9(2) . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30B 109.0 . . ? C31 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C32 C31 C30 113.2(2) . . ? C32 C31 H31A 108.9 . . ? C30 C31 H31A 108.9 . . ? C32 C31 H31B 108.9 . . ? C30 C31 H31B 108.9 . . ? H31A C31 H31B 107.8 . . ? O8 C32 C31 108.5(2) . . ? O8 C32 H32A 110.0 . . ? C31 C32 H32A 110.0 . . ? O8 C32 H32B 110.0 . . ? C31 C32 H32B 110.0 . . ? H32A C32 H32B 108.4 . . ? O9 C33 O8 124.3(3) . . ? O9 C33 C34 125.1(3) . . ? O8 C33 C34 110.7(3) . . ? C35 C34 C35A 52.8(5) . . ? C35 C34 C33 114.7(4) . . ? C35A C34 C33 114.7(5) . . ? C35 C34 H34A 108.6 . . ? C35A C34 H34A 58.4 . . ? C33 C34 H34A 108.6 . . ? C35 C34 H34B 108.6 . . ? C35A C34 H34B 136.7 . . ? C33 C34 H34B 108.6 . . ? H34A C34 H34B 107.6 . . ? C35 C34 H34C 136.7 . . ? C35A C34 H34C 108.6 . . ? C33 C34 H34C 108.6 . . ? H34A C34 H34C 55.3 . . ? H34B C34 H34C 54.7 . . ? C35 C34 H34D 58.4 . . ? C35A C34 H34D 108.6 . . ? C33 C34 H34D 108.6 . . ? H34A C34 H34D 142.5 . . ? H34B C34 H34D 55.3 . . ? H34C C34 H34D 107.6 . . ? C34 C35 H35A 109.5 . . ? C34 C35 H35B 109.5 . . ? C34 C35 H35C 109.5 . . ? C34 C35A H35D 109.5 . . ? C34 C35A H35E 109.5 . . ? H35D C35A H35E 109.5 . . ? C34 C35A H35F 109.5 . . ? H35D C35A H35F 109.5 . . ? H35E C35A H35F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.817 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.054 data_121023_zb_267 _database_code_depnum_ccdc_archive 'CCDC 915062' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 O7, C18 H30 N O2, F6 P' _chemical_formula_sum 'C36 H58 F6 N O9 P' _chemical_formula_weight 793.80 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.9587(8) _cell_length_b 15.3868(9) _cell_length_c 19.5493(12) _cell_angle_alpha 90.00 _cell_angle_beta 92.997(6) _cell_angle_gamma 90.00 _cell_volume 3892.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 3958 _cell_measurement_theta_min 3.2195 _cell_measurement_theta_max 29.6061 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9430 _exptl_absorpt_correction_T_max 0.9529 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16009 _diffrn_reflns_av_R_equivalents 0.0274 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7118 _reflns_number_gt 5167 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0431P)^2^+2.1477P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7118 _refine_ls_number_parameters 484 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.0990 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 P1 P 1.23160(5) 0.91295(4) 0.08112(3) 0.03332(16) Uani 1 1 d . . . F1 F 1.20638(12) 0.89247(10) 0.00201(7) 0.0547(4) Uani 1 1 d . . . F2 F 1.34968(12) 0.92586(14) 0.06561(8) 0.0757(6) Uani 1 1 d . . . F3 F 1.25675(14) 0.93313(13) 0.15972(8) 0.0746(5) Uani 1 1 d . . . F4 F 1.11473(11) 0.89859(10) 0.09712(9) 0.0588(4) Uani 1 1 d . . . F5 F 1.25204(13) 0.81201(10) 0.09412(8) 0.0666(5) Uani 1 1 d . . . F6 F 1.20922(16) 1.01285(10) 0.06662(10) 0.0760(5) Uani 1 1 d . . . O1 O 0.86695(11) 1.06445(9) 0.47070(7) 0.0286(3) Uani 1 1 d . . . O2 O 0.80273(11) 0.88271(9) 0.44306(7) 0.0286(3) Uani 1 1 d . . . O3 O 0.79650(11) 0.77756(9) 0.31605(7) 0.0291(3) Uani 1 1 d . . . O4 O 0.81426(11) 0.83819(9) 0.17938(7) 0.0322(4) Uani 1 1 d . . . O5 O 0.93695(11) 0.98587(9) 0.15527(7) 0.0314(4) Uani 1 1 d . . . O6 O 1.00344(11) 1.13345(9) 0.24427(7) 0.0321(4) Uani 1 1 d . . . O7 O 0.96550(11) 1.16596(9) 0.38844(7) 0.0285(3) Uani 1 1 d . . . O8 O 1.05281(13) 0.65253(11) 0.19267(9) 0.0473(4) Uani 1 1 d . . . O9 O 1.16673(18) 0.59203(17) 0.12548(13) 0.0881(8) Uani 1 1 d . . . N1 N 0.88585(13) 0.94544(10) 0.29271(8) 0.0241(4) Uani 1 1 d . . . H1A H 0.8573 0.8911 0.2969 0.029 Uiso 1 1 calc R . . H1B H 0.8993 0.9533 0.2474 0.029 Uiso 1 1 calc R . . C1 C 0.91345(16) 1.20687(13) 0.43876(11) 0.0271(5) Uani 1 1 d . . . C2 C 0.91261(18) 1.29598(14) 0.44895(12) 0.0360(5) Uani 1 1 d . . . H2 H 0.9518 1.3327 0.4211 0.043 Uiso 1 1 calc R . . C3 C 0.8546(2) 1.33177(15) 0.49977(13) 0.0416(6) Uani 1 1 d . . . H3 H 0.8548 1.3929 0.5067 0.050 Uiso 1 1 calc R . . C4 C 0.7976(2) 1.27967(16) 0.53986(12) 0.0417(6) Uani 1 1 d . . . H4 H 0.7570 1.3047 0.5738 0.050 Uiso 1 1 calc R . . C5 C 0.79883(18) 1.18954(15) 0.53087(11) 0.0358(5) Uani 1 1 d . . . H5 H 0.7590 1.1534 0.5588 0.043 Uiso 1 1 calc R . . C6 C 0.85777(16) 1.15277(13) 0.48163(11) 0.0278(5) Uani 1 1 d . . . C7 C 0.81395(18) 1.00825(13) 0.51563(11) 0.0301(5) Uani 1 1 d . . . H7A H 0.7384 1.0131 0.5059 0.036 Uiso 1 1 calc R . . H7B H 0.8295 1.0258 0.5638 0.036 Uiso 1 1 calc R . . C8 C 0.84743(17) 0.91651(14) 0.50558(10) 0.0297(5) Uani 1 1 d . . . H8A H 0.9237 0.9141 0.5048 0.036 Uiso 1 1 calc R . . H8B H 0.8261 0.8804 0.5443 0.036 Uiso 1 1 calc R . . C9 C 0.81939(19) 0.79092(13) 0.43848(11) 0.0334(5) Uani 1 1 d . . . H9A H 0.8008 0.7624 0.4815 0.040 Uiso 1 1 calc R . . H9B H 0.8932 0.7791 0.4316 0.040 Uiso 1 1 calc R . . C10 C 0.75420(19) 0.75521(14) 0.37954(11) 0.0349(5) Uani 1 1 d . . . H10A H 0.7502 0.6912 0.3836 0.042 Uiso 1 1 calc R . . H10B H 0.6832 0.7788 0.3808 0.042 Uiso 1 1 calc R . . C11 C 0.73010(17) 0.75080(14) 0.25887(11) 0.0328(5) Uani 1 1 d . . . H11A H 0.6709 0.7912 0.2530 0.039 Uiso 1 1 calc R . . H11B H 0.7029 0.6918 0.2672 0.039 Uiso 1 1 calc R . . C12 C 0.79029(18) 0.75066(14) 0.19573(11) 0.0331(5) Uani 1 1 d . . . H12A H 0.8547 0.7167 0.2037 0.040 Uiso 1 1 calc R . . H12B H 0.7490 0.7237 0.1573 0.040 Uiso 1 1 calc R . . C13 C 0.87493(18) 0.84522(15) 0.12104(11) 0.0348(5) Uani 1 1 d . . . H13A H 0.8423 0.8116 0.0825 0.042 Uiso 1 1 calc R . . H13B H 0.9447 0.8210 0.1318 0.042 Uiso 1 1 calc R . . C14 C 0.88331(18) 0.93834(15) 0.10123(11) 0.0359(5) Uani 1 1 d . . . H14A H 0.9212 0.9432 0.0587 0.043 Uiso 1 1 calc R . . H14B H 0.8134 0.9631 0.0923 0.043 Uiso 1 1 calc R . . C15 C 0.97447(18) 1.06778(14) 0.13297(11) 0.0356(5) Uani 1 1 d . . . H15A H 0.9161 1.1090 0.1264 0.043 Uiso 1 1 calc R . . H15B H 1.0065 1.0606 0.0885 0.043 Uiso 1 1 calc R . . C16 C 1.05243(18) 1.10385(15) 0.18456(12) 0.0353(5) Uani 1 1 d . . . H16A H 1.1038 1.0584 0.1977 0.042 Uiso 1 1 calc R . . H16B H 1.0895 1.1528 0.1640 0.042 Uiso 1 1 calc R . . C17 C 1.07687(17) 1.16828(15) 0.29397(12) 0.0344(5) Uani 1 1 d . . . H17A H 1.1272 1.2049 0.2708 0.041 Uiso 1 1 calc R . . H17B H 1.1152 1.1201 0.3173 0.041 Uiso 1 1 calc R . . C18 C 1.02439(17) 1.22145(14) 0.34577(11) 0.0327(5) Uani 1 1 d . . . H18A H 1.0767 1.2537 0.3745 0.039 Uiso 1 1 calc R . . H18B H 0.9779 1.2643 0.3222 0.039 Uiso 1 1 calc R . . C19 C 0.62622(16) 0.95437(13) 0.30646(11) 0.0281(5) Uani 1 1 d . . . H19 H 0.6373 0.9349 0.3524 0.034 Uiso 1 1 calc R . . C20 C 0.53121(17) 0.93883(13) 0.27177(11) 0.0296(5) Uani 1 1 d . . . C21 C 0.51606(17) 0.96882(13) 0.20519(11) 0.0308(5) Uani 1 1 d . . . H21 H 0.4514 0.9587 0.1813 0.037 Uiso 1 1 calc R . . C22 C 0.59259(17) 1.01324(13) 0.17223(11) 0.0286(5) Uani 1 1 d . . . C23 C 0.68702(16) 1.02649(13) 0.20777(11) 0.0268(5) Uani 1 1 d . . . H23 H 0.7406 1.0558 0.1857 0.032 Uiso 1 1 calc R . . C24 C 0.70508(16) 0.99791(12) 0.27490(10) 0.0242(5) Uani 1 1 d . . . C25 C 0.44662(19) 0.89013(17) 0.30570(13) 0.0455(6) Uani 1 1 d . . . H25A H 0.4707 0.8315 0.3178 0.068 Uiso 1 1 calc R . . H25B H 0.3856 0.8863 0.2741 0.068 Uiso 1 1 calc R . . H25C H 0.4287 0.9210 0.3473 0.068 Uiso 1 1 calc R . . C26 C 0.57294(19) 1.04744(17) 0.10041(12) 0.0425(6) Uani 1 1 d . . . H26A H 0.5207 1.0113 0.0760 0.064 Uiso 1 1 calc R . . H26B H 0.6373 1.0457 0.0762 0.064 Uiso 1 1 calc R . . H26C H 0.5481 1.1075 0.1023 0.064 Uiso 1 1 calc R . . C27 C 0.80838(16) 1.01197(13) 0.31240(11) 0.0262(5) Uani 1 1 d . . . H27A H 0.8343 1.0707 0.3018 0.031 Uiso 1 1 calc R . . H27B H 0.7999 1.0088 0.3624 0.031 Uiso 1 1 calc R . . C28 C 0.98577(16) 0.94831(13) 0.33444(10) 0.0266(5) Uani 1 1 d . . . H28A H 0.9760 0.9218 0.3798 0.032 Uiso 1 1 calc R . . H28B H 1.0064 1.0097 0.3419 0.032 Uiso 1 1 calc R . . C29 C 1.07177(16) 0.90038(14) 0.29992(11) 0.0294(5) Uani 1 1 d . . . H29A H 1.0791 0.9258 0.2539 0.035 Uiso 1 1 calc R . . H29B H 1.1375 0.9104 0.3269 0.035 Uiso 1 1 calc R . . C30 C 1.05549(16) 0.80317(14) 0.29210(11) 0.0306(5) Uani 1 1 d . . . H30A H 0.9941 0.7927 0.2609 0.037 Uiso 1 1 calc R . . H30B H 1.0413 0.7781 0.3373 0.037 Uiso 1 1 calc R . . C31 C 1.14836(18) 0.75695(15) 0.26407(13) 0.0382(6) Uani 1 1 d . . . H31A H 1.1670 0.7862 0.2213 0.046 Uiso 1 1 calc R . . H31B H 1.2079 0.7625 0.2977 0.046 Uiso 1 1 calc R . . C32 C 1.1294(2) 0.66161(16) 0.24922(14) 0.0461(6) Uani 1 1 d . . . H32A H 1.1948 0.6334 0.2373 0.055 Uiso 1 1 calc R . . H32B H 1.1046 0.6326 0.2905 0.055 Uiso 1 1 calc R . . C33 C 1.0805(2) 0.61638(17) 0.13398(15) 0.0537(8) Uani 1 1 d . A . C34 C 0.9913(3) 0.60783(18) 0.08257(14) 0.0591(8) Uani 1 1 d D . . H34A H 0.9366 0.6485 0.0959 0.071 Uiso 0.828(4) 1 calc PR A 1 H34B H 0.9632 0.5483 0.0863 0.071 Uiso 0.828(4) 1 calc PR A 1 H34C H 0.9258 0.6345 0.0960 0.071 Uiso 0.172(4) 1 calc PR A 2 H34D H 0.9808 0.5491 0.0628 0.071 Uiso 0.172(4) 1 calc PR A 2 C35 C 1.0109(3) 0.6244(2) 0.00731(16) 0.0499(9) Uani 0.828(4) 1 d PD A 1 H35A H 1.0758 0.5950 -0.0040 0.060 Uiso 0.828(4) 1 calc PR A 1 H35B H 0.9539 0.5985 -0.0216 0.060 Uiso 0.828(4) 1 calc PR A 1 C36 C 1.0189(3) 0.7174(2) -0.00920(18) 0.0798(10) Uani 1 1 d D . . H36A H 1.0159 0.7249 -0.0590 0.120 Uiso 0.828(4) 1 calc PR A 1 H36B H 1.0846 0.7403 0.0103 0.120 Uiso 0.828(4) 1 calc PR A 1 H36C H 0.9615 0.7489 0.0101 0.120 Uiso 0.828(4) 1 calc PR A 1 H36D H 0.9506 0.6933 -0.0220 0.120 Uiso 0.172(4) 1 calc PR A 2 H36E H 1.0619 0.7160 -0.0489 0.120 Uiso 0.172(4) 1 calc PR A 2 H36F H 1.0114 0.7776 0.0061 0.120 Uiso 0.172(4) 1 calc PR A 2 C35A C 1.0644(11) 0.6693(9) 0.0425(7) 0.0499(9) Uani 0.172(4) 1 d PD A 2 H35C H 1.0990 0.7096 0.0758 0.060 Uiso 0.172(4) 1 calc PR A 2 H35D H 1.1188 0.6331 0.0231 0.060 Uiso 0.172(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0270(3) 0.0418(3) 0.0315(3) 0.0010(3) 0.0038(2) -0.0019(3) F1 0.0587(10) 0.0662(10) 0.0381(8) -0.0023(7) -0.0086(7) 0.0024(8) F2 0.0341(9) 0.1417(17) 0.0521(10) -0.0064(10) 0.0107(7) -0.0220(10) F3 0.0698(12) 0.1215(15) 0.0328(9) -0.0136(9) 0.0056(8) -0.0229(11) F4 0.0306(8) 0.0601(10) 0.0872(12) -0.0019(8) 0.0167(8) -0.0007(7) F5 0.0742(12) 0.0580(10) 0.0687(11) 0.0183(8) 0.0129(9) 0.0308(9) F6 0.1113(15) 0.0367(8) 0.0817(13) 0.0018(8) 0.0228(11) -0.0090(9) O1 0.0335(9) 0.0262(7) 0.0265(8) -0.0025(6) 0.0052(6) -0.0022(6) O2 0.0374(9) 0.0230(7) 0.0249(8) -0.0002(6) -0.0034(6) -0.0023(6) O3 0.0295(8) 0.0288(8) 0.0288(8) -0.0040(6) -0.0016(6) -0.0052(6) O4 0.0357(9) 0.0318(8) 0.0290(8) -0.0071(7) 0.0016(7) 0.0017(7) O5 0.0368(9) 0.0347(8) 0.0228(8) 0.0022(6) 0.0016(6) 0.0023(7) O6 0.0261(8) 0.0395(8) 0.0311(8) -0.0009(7) 0.0053(6) -0.0010(7) O7 0.0293(8) 0.0244(7) 0.0321(8) -0.0002(6) 0.0029(6) -0.0043(6) O8 0.0456(11) 0.0432(10) 0.0543(11) -0.0172(8) 0.0137(9) 0.0000(8) O9 0.0684(16) 0.1102(19) 0.0890(18) -0.0280(15) 0.0374(13) 0.0145(14) N1 0.0266(10) 0.0244(9) 0.0210(9) -0.0018(7) -0.0022(7) -0.0005(7) C1 0.0245(11) 0.0278(11) 0.0279(11) -0.0043(9) -0.0073(9) 0.0023(9) C2 0.0375(14) 0.0299(12) 0.0397(14) -0.0022(10) -0.0078(11) -0.0025(10) C3 0.0498(16) 0.0300(12) 0.0432(14) -0.0107(11) -0.0133(12) 0.0074(11) C4 0.0495(16) 0.0408(13) 0.0343(13) -0.0115(11) -0.0032(11) 0.0143(12) C5 0.0381(14) 0.0397(13) 0.0292(12) -0.0022(10) -0.0018(10) 0.0049(11) C6 0.0280(12) 0.0266(11) 0.0279(11) -0.0044(9) -0.0074(9) 0.0012(9) C7 0.0352(13) 0.0337(12) 0.0216(11) -0.0025(9) 0.0021(9) -0.0060(10) C8 0.0330(12) 0.0332(11) 0.0225(11) 0.0040(9) -0.0027(9) -0.0038(10) C9 0.0446(14) 0.0231(11) 0.0329(12) 0.0042(9) 0.0050(10) -0.0009(10) C10 0.0429(14) 0.0254(11) 0.0370(13) -0.0012(10) 0.0089(11) -0.0097(10) C11 0.0298(12) 0.0271(11) 0.0408(13) -0.0078(10) -0.0055(10) -0.0030(10) C12 0.0348(13) 0.0293(11) 0.0343(13) -0.0107(10) -0.0080(10) 0.0012(10) C13 0.0355(13) 0.0429(13) 0.0256(12) -0.0101(10) -0.0036(10) 0.0047(11) C14 0.0360(13) 0.0486(14) 0.0226(11) -0.0032(11) -0.0035(9) 0.0078(11) C15 0.0433(14) 0.0356(12) 0.0287(12) 0.0067(10) 0.0095(10) 0.0082(11) C16 0.0354(13) 0.0346(12) 0.0374(13) 0.0067(10) 0.0154(10) 0.0011(10) C17 0.0248(12) 0.0385(12) 0.0400(13) 0.0075(11) 0.0020(10) -0.0063(10) C18 0.0303(12) 0.0292(11) 0.0380(13) 0.0033(10) -0.0034(10) -0.0089(10) C19 0.0329(13) 0.0250(10) 0.0265(11) -0.0004(9) 0.0040(9) 0.0053(9) C20 0.0286(12) 0.0253(11) 0.0352(12) -0.0016(10) 0.0055(10) 0.0004(9) C21 0.0263(12) 0.0285(11) 0.0371(13) -0.0050(10) -0.0045(10) 0.0012(9) C22 0.0289(12) 0.0262(11) 0.0304(12) -0.0014(9) -0.0031(9) 0.0034(9) C23 0.0276(12) 0.0240(10) 0.0290(12) 0.0009(9) 0.0014(9) 0.0011(9) C24 0.0260(11) 0.0204(10) 0.0262(11) -0.0034(9) 0.0002(9) 0.0028(8) C25 0.0388(15) 0.0505(15) 0.0476(16) 0.0016(12) 0.0080(12) -0.0093(12) C26 0.0400(15) 0.0505(15) 0.0356(14) 0.0082(12) -0.0106(11) -0.0046(12) C27 0.0318(12) 0.0215(10) 0.0249(11) -0.0032(9) -0.0021(9) 0.0029(9) C28 0.0281(12) 0.0253(10) 0.0256(11) -0.0004(9) -0.0065(9) -0.0013(9) C29 0.0265(12) 0.0333(11) 0.0281(12) 0.0011(9) -0.0027(9) -0.0012(9) C30 0.0257(12) 0.0315(11) 0.0350(12) 0.0009(10) 0.0050(9) 0.0001(9) C31 0.0334(13) 0.0374(13) 0.0444(14) 0.0004(11) 0.0072(11) 0.0024(10) C32 0.0382(15) 0.0377(13) 0.0631(18) -0.0048(12) 0.0114(13) 0.0074(11) C33 0.065(2) 0.0378(14) 0.0619(19) -0.0068(13) 0.0371(16) -0.0055(13) C34 0.088(2) 0.0436(15) 0.0470(17) -0.0070(13) 0.0175(16) -0.0044(15) C35 0.055(2) 0.0517(19) 0.0447(19) -0.0159(15) 0.0158(15) -0.0042(15) C36 0.091(3) 0.080(2) 0.072(2) 0.0029(19) 0.037(2) 0.001(2) C35A 0.055(2) 0.0517(19) 0.0447(19) -0.0159(15) 0.0158(15) -0.0042(15) _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 P1 F4 1.5779(15) . ? P1 F3 1.5848(16) . ? P1 F6 1.5871(17) . ? P1 F2 1.5879(16) . ? P1 F5 1.5936(16) . ? P1 F1 1.5953(15) . ? O1 C6 1.382(2) . ? O1 C7 1.433(2) . ? O2 C8 1.423(2) . ? O2 C9 1.432(2) . ? O3 C10 1.425(3) . ? O3 C11 1.435(2) . ? O4 C12 1.422(3) . ? O4 C13 1.423(3) . ? O5 C15 1.427(3) . ? O5 C14 1.434(3) . ? O6 C17 1.428(3) . ? O6 C16 1.432(3) . ? O7 C1 1.374(2) . ? O7 C18 1.440(2) . ? O8 C33 1.341(3) . ? O8 C32 1.454(3) . ? O9 C33 1.198(3) . ? N1 C28 1.495(3) . ? N1 C27 1.498(3) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? C1 C2 1.386(3) . ? C1 C6 1.407(3) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.366(4) . ? C3 H3 0.9500 . ? C4 C5 1.398(3) . ? C4 H4 0.9500 . ? C5 C6 1.381(3) . ? C5 H5 0.9500 . ? C7 C8 1.493(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.497(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.494(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.490(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.496(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.493(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C24 1.393(3) . ? C19 C20 1.395(3) . ? C19 H19 0.9500 . ? C20 C21 1.385(3) . ? C20 C25 1.510(3) . ? C21 C22 1.390(3) . ? C21 H21 0.9500 . ? C22 C23 1.390(3) . ? C22 C26 1.508(3) . ? C23 C24 1.392(3) . ? C23 H23 0.9500 . ? C24 C27 1.508(3) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.523(3) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.517(3) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.524(3) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.513(3) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 C34 1.498(4) . ? C34 C35 1.528(4) . ? C34 C35A 1.576(12) . ? C34 H34A 0.9900 . ? C34 H34B 0.9900 . ? C34 H34C 0.9900 . ? C34 H34D 0.9900 . ? C35 C36 1.471(4) . ? C35 H35A 0.9900 . ? C35 H35B 0.9900 . ? C36 C35A 1.362(13) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C36 H36D 0.9800 . ? C36 H36E 0.9800 . ? C36 H36F 0.9800 . ? C35A H35C 0.9900 . ? C35A H35D 0.9900 . ? 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 F4 P1 F3 89.20(9) . . ? F4 P1 F6 90.15(9) . . ? F3 P1 F6 90.56(11) . . ? F4 P1 F2 179.03(11) . . ? F3 P1 F2 90.53(9) . . ? F6 P1 F2 90.78(11) . . ? F4 P1 F5 89.15(9) . . ? F3 P1 F5 90.70(10) . . ? F6 P1 F5 178.55(11) . . ? F2 P1 F5 89.92(10) . . ? F4 P1 F1 90.83(9) . . ? F3 P1 F1 179.90(12) . . ? F6 P1 F1 89.54(9) . . ? F2 P1 F1 89.44(9) . . ? F5 P1 F1 89.20(9) . . ? C6 O1 C7 116.80(16) . . ? C8 O2 C9 110.98(15) . . ? C10 O3 C11 111.54(16) . . ? C12 O4 C13 112.86(16) . . ? C15 O5 C14 112.65(16) . . ? C17 O6 C16 111.46(16) . . ? C1 O7 C18 115.97(15) . . ? C33 O8 C32 119.2(2) . . ? C28 N1 C27 114.36(15) . . ? C28 N1 H1A 108.7 . . ? C27 N1 H1A 108.7 . . ? C28 N1 H1B 108.7 . . ? C27 N1 H1B 108.7 . . ? H1A N1 H1B 107.6 . . ? O7 C1 C2 124.3(2) . . ? O7 C1 C6 116.21(17) . . ? C2 C1 C6 119.5(2) . . ? C1 C2 C3 120.2(2) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.5(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.0(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.3(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 O1 124.5(2) . . ? C5 C6 C1 119.50(19) . . ? O1 C6 C1 116.04(18) . . ? O1 C7 C8 109.75(17) . . ? O1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? O1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? O2 C8 C7 110.51(17) . . ? O2 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C10 109.22(18) . . ? O2 C9 H9A 109.8 . . ? C10 C9 H9A 109.8 . . ? O2 C9 H9B 109.8 . . ? C10 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? O3 C10 C9 110.77(18) . . ? O3 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O3 C11 C12 109.05(17) . . ? O3 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O3 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O4 C12 C11 108.30(17) . . ? O4 C12 H12A 110.0 . . ? C11 C12 H12A 110.0 . . ? O4 C12 H12B 110.0 . . ? C11 C12 H12B 110.0 . . ? H12A C12 H12B 108.4 . . ? O4 C13 C14 109.42(18) . . ? O4 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? O4 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? O5 C14 C13 109.76(17) . . ? O5 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? O5 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? O5 C15 C16 110.52(17) . . ? O5 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? O6 C16 C15 110.79(18) . . ? O6 C16 H16A 109.5 . . ? C15 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 108.1 . . ? O6 C17 C18 110.86(18) . . ? O6 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? O6 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? O7 C18 C17 109.99(17) . . ? O7 C18 H18A 109.7 . . ? C17 C18 H18A 109.7 . . ? O7 C18 H18B 109.7 . . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C24 C19 C20 121.1(2) . . ? C24 C19 H19 119.4 . . ? C20 C19 H19 119.4 . . ? C21 C20 C19 118.5(2) . . ? C21 C20 C25 120.5(2) . . ? C19 C20 C25 121.0(2) . . ? C20 C21 C22 122.0(2) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C23 118.1(2) . . ? C21 C22 C26 120.9(2) . . ? C23 C22 C26 121.0(2) . . ? C22 C23 C24 121.7(2) . . ? C22 C23 H23 119.2 . . ? C24 C23 H23 119.2 . . ? C23 C24 C19 118.58(19) . . ? C23 C24 C27 120.95(19) . . ? C19 C24 C27 120.46(19) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N1 C27 C24 111.51(16) . . ? N1 C27 H27A 109.3 . . ? C24 C27 H27A 109.3 . . ? N1 C27 H27B 109.3 . . ? C24 C27 H27B 109.3 . . ? H27A C27 H27B 108.0 . . ? N1 C28 C29 112.15(16) . . ? N1 C28 H28A 109.2 . . ? C29 C28 H28A 109.2 . . ? N1 C28 H28B 109.2 . . ? C29 C28 H28B 109.2 . . ? H28A C28 H28B 107.9 . . ? C30 C29 C28 114.89(18) . . ? C30 C29 H29A 108.5 . . ? C28 C29 H29A 108.5 . . ? C30 C29 H29B 108.5 . . ? C28 C29 H29B 108.5 . . ? H29A C29 H29B 107.5 . . ? C29 C30 C31 112.83(18) . . ? C29 C30 H30A 109.0 . . ? C31 C30 H30A 109.0 . . ? C29 C30 H30B 109.0 . . ? C31 C30 H30B 109.0 . . ? H30A C30 H30B 107.8 . . ? C32 C31 C30 113.47(19) . . ? C32 C31 H31A 108.9 . . ? C30 C31 H31A 108.9 . . ? C32 C31 H31B 108.9 . . ? C30 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? O8 C32 C31 109.7(2) . . ? O8 C32 H32A 109.7 . . ? C31 C32 H32A 109.7 . . ? O8 C32 H32B 109.7 . . ? C31 C32 H32B 109.7 . . ? H32A C32 H32B 108.2 . . ? O9 C33 O8 122.8(3) . . ? O9 C33 C34 124.9(3) . . ? O8 C33 C34 112.3(2) . . ? C33 C34 C35 118.0(3) . . ? C33 C34 C35A 79.5(6) . . ? C35 C34 C35A 44.4(6) . . ? C33 C34 H34A 107.8 . . ? C35 C34 H34A 107.8 . . ? C35A C34 H34A 102.1 . . ? C33 C34 H34B 107.8 . . ? C35 C34 H34B 107.8 . . ? C35A C34 H34B 145.5 . . ? H34A C34 H34B 107.1 . . ? C33 C34 H34C 115.3 . . ? C35 C34 H34C 111.9 . . ? C35A C34 H34C 115.3 . . ? H34A C34 H34C 14.8 . . ? H34B C34 H34C 92.4 . . ? C33 C34 H34D 115.3 . . ? C35 C34 H34D 78.7 . . ? C35A C34 H34D 115.3 . . ? H34A C34 H34D 126.4 . . ? H34B C34 H34D 30.6 . . ? H34C C34 H34D 112.4 . . ? C36 C35 C34 113.0(3) . . ? C36 C35 H35A 109.0 . . ? C34 C35 H35A 109.0 . . ? C36 C35 H35B 109.0 . . ? C34 C35 H35B 109.0 . . ? H35A C35 H35B 107.8 . . ? C35A C36 C35 48.8(6) . . ? C35A C36 H36A 142.7 . . ? C35 C36 H36A 109.5 . . ? C35A C36 H36B 64.7 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35A C36 H36C 106.9 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C35A C36 H36D 109.5 . . ? C35 C36 H36D 67.4 . . ? H36A C36 H36D 78.7 . . ? H36B C36 H36D 171.8 . . ? H36C C36 H36D 65.9 . . ? C35A C36 H36E 109.5 . . ? C35 C36 H36E 101.6 . . ? H36A C36 H36E 37.7 . . ? H36B C36 H36E 78.4 . . ? H36C C36 H36E 142.3 . . ? H36D C36 H36E 109.5 . . ? C35A C36 H36F 109.5 . . ? C35 C36 H36F 147.5 . . ? H36A C36 H36F 101.1 . . ? H36B C36 H36F 68.8 . . ? H36C C36 H36F 47.6 . . ? H36D C36 H36F 109.5 . . ? H36E C36 H36F 109.5 . . ? C36 C35A C34 116.6(10) . . ? C36 C35A H35C 108.2 . . ? C34 C35A H35C 108.2 . . ? C36 C35A H35D 108.2 . . ? C34 C35A H35D 108.2 . . ? H35C C35A H35D 107.3 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.505 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.046 data_121023_zb_268 _database_code_depnum_ccdc_archive 'CCDC 915063' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 O7, C18 H30 N O2, F6 P' _chemical_formula_sum 'C36 H58 F6 N O9 P' _chemical_formula_weight 793.80 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.3855(6) _cell_length_b 21.1336(13) _cell_length_c 20.3716(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.470(5) _cell_angle_gamma 90.00 _cell_volume 4015.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 3720 _cell_measurement_theta_min 2.9947 _cell_measurement_theta_max 29.5960 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 0.148 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9447 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19987 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0419 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.35 _reflns_number_total 7325 _reflns_number_gt 4802 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0758P)^2^+4.9524P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7325 _refine_ls_number_parameters 486 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.1074 _refine_ls_R_factor_gt 0.0694 _refine_ls_wR_factor_ref 0.1922 _refine_ls_wR_factor_gt 0.1663 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 P1 P 0.21795(11) 0.23589(5) 0.05147(6) 0.0563(3) Uani 1 1 d . . . F1 F 0.2584(4) 0.25014(14) 0.12737(15) 0.1165(12) Uani 1 1 d . . . F2 F 0.0548(3) 0.24012(17) 0.0623(2) 0.1320(14) Uani 1 1 d . . . F3 F 0.2162(3) 0.30921(12) 0.03431(16) 0.0983(10) Uani 1 1 d . . . F4 F 0.1724(4) 0.21926(14) -0.02348(14) 0.1069(11) Uani 1 1 d . . . F5 F 0.3779(3) 0.22968(19) 0.0418(2) 0.1372(15) Uani 1 1 d . . . F6 F 0.2154(4) 0.16262(12) 0.06810(14) 0.0920(9) Uani 1 1 d . . . O1 O 0.6801(2) 0.10316(10) 0.09940(11) 0.0406(6) Uani 1 1 d . . . O2 O 0.6794(3) 0.15810(11) 0.23249(12) 0.0472(6) Uani 1 1 d . . . O3 O 0.6229(3) 0.08612(12) 0.35203(11) 0.0511(6) Uani 1 1 d . . . O4 O 0.6116(3) -0.04847(12) 0.37359(11) 0.0476(6) Uani 1 1 d . . . O5 O 0.5594(2) -0.14909(11) 0.27564(11) 0.0433(6) Uani 1 1 d . . . O6 O 0.5941(2) -0.12660(10) 0.14170(10) 0.0353(5) Uani 1 1 d . . . O7 O 0.6389(2) -0.01494(10) 0.05945(10) 0.0351(5) Uani 1 1 d . . . O8 O 0.1557(4) 0.17670(15) 0.3122(2) 0.0924(12) Uani 1 1 d . A . O9 O 0.0410(4) 0.1135(2) 0.3759(2) 0.1079(14) Uani 1 1 d . A . N1 N 0.6217(2) -0.02084(12) 0.23216(12) 0.0304(6) Uani 1 1 d . . . H1A H 0.6212 -0.0258 0.2770 0.037 Uiso 1 1 calc R . . H1B H 0.6073 -0.0601 0.2130 0.037 Uiso 1 1 calc R . . C1 C 0.7278(3) 0.02135(16) 0.02532(15) 0.0352(7) Uani 1 1 d . . . C2 C 0.7932(3) -0.00045(18) -0.02814(16) 0.0435(8) Uani 1 1 d . . . H2 H 0.7769 -0.0426 -0.0433 0.052 Uiso 1 1 calc R . . C3 C 0.7657(3) 0.00291(15) 0.21919(16) 0.0353(7) Uani 1 1 d . . . H3A H 0.7791 0.0466 0.2363 0.042 Uiso 1 1 calc R . . H3B H 0.7714 0.0039 0.1710 0.042 Uiso 1 1 calc R . . C4 C 0.8825(4) 0.0392(2) -0.05958(18) 0.0556(10) Uani 1 1 d . . . H4 H 0.9271 0.0240 -0.0961 0.067 Uiso 1 1 calc R . . C5 C 0.9062(4) 0.1000(2) -0.03800(19) 0.0593(11) Uani 1 1 d . . . H5 H 0.9677 0.1267 -0.0595 0.071 Uiso 1 1 calc R . . C6 C 0.8409(4) 0.12280(19) 0.01510(18) 0.0518(10) Uani 1 1 d . . . H6 H 0.8578 0.1651 0.0297 0.062 Uiso 1 1 calc R . . C7 C 0.7510(3) 0.08408(16) 0.04700(15) 0.0387(8) Uani 1 1 d . . . C8 C 0.6928(4) 0.16868(16) 0.11651(19) 0.0509(9) Uani 1 1 d . . . H8A H 0.6571 0.1949 0.0778 0.061 Uiso 1 1 calc R . . H8B H 0.7949 0.1794 0.1292 0.061 Uiso 1 1 calc R . . C9 C 0.6083(4) 0.18285(17) 0.17261(19) 0.0520(10) Uani 1 1 d . . . H9A H 0.5968 0.2292 0.1767 0.062 Uiso 1 1 calc R . . H9B H 0.5117 0.1638 0.1639 0.062 Uiso 1 1 calc R . . C10 C 0.6188(4) 0.18095(18) 0.2889(2) 0.0531(10) Uani 1 1 d . . . H10A H 0.5139 0.1739 0.2830 0.064 Uiso 1 1 calc R . . H10B H 0.6362 0.2270 0.2935 0.064 Uiso 1 1 calc R . . C11 C 0.6833(4) 0.1479(2) 0.34997(19) 0.0564(10) Uani 1 1 d . . . H11A H 0.7885 0.1448 0.3499 0.068 Uiso 1 1 calc R . . H11B H 0.6636 0.1722 0.3895 0.068 Uiso 1 1 calc R . . C12 C 0.6589(5) 0.0566(2) 0.41455(17) 0.0591(11) Uani 1 1 d . . . H12A H 0.6402 0.0860 0.4504 0.071 Uiso 1 1 calc R . . H12B H 0.7621 0.0456 0.4203 0.071 Uiso 1 1 calc R . . C13 C 0.5716(5) -0.0015(2) 0.41816(17) 0.0582(11) Uani 1 1 d . . . H13A H 0.5850 -0.0183 0.4638 0.070 Uiso 1 1 calc R . . H13B H 0.4689 0.0091 0.4072 0.070 Uiso 1 1 calc R . . C14 C 0.5452(5) -0.1080(2) 0.38324(19) 0.0589(11) Uani 1 1 d . . . H14A H 0.4409 -0.1051 0.3692 0.071 Uiso 1 1 calc R . . H14B H 0.5589 -0.1194 0.4307 0.071 Uiso 1 1 calc R . . C15 C 0.6101(5) -0.15759(19) 0.34383(18) 0.0552(10) Uani 1 1 d . . . H15A H 0.7159 -0.1541 0.3504 0.066 Uiso 1 1 calc R . . H15B H 0.5830 -0.2001 0.3586 0.066 Uiso 1 1 calc R . . C16 C 0.6196(4) -0.19417(16) 0.23559(17) 0.0439(8) Uani 1 1 d . . . H16A H 0.6016 -0.2375 0.2513 0.053 Uiso 1 1 calc R . . H16B H 0.7246 -0.1878 0.2379 0.053 Uiso 1 1 calc R . . C17 C 0.5520(4) -0.18610(15) 0.16604(17) 0.0414(8) Uani 1 1 d . . . H17A H 0.5830 -0.2207 0.1381 0.050 Uiso 1 1 calc R . . H17B H 0.4463 -0.1879 0.1646 0.050 Uiso 1 1 calc R . . C18 C 0.5206(3) -0.11321(15) 0.07720(15) 0.0368(7) Uani 1 1 d . . . H18A H 0.4346 -0.0872 0.0818 0.044 Uiso 1 1 calc R . . H18B H 0.4886 -0.1533 0.0552 0.044 Uiso 1 1 calc R . . C19 C 0.6167(4) -0.07884(15) 0.03591(15) 0.0371(7) Uani 1 1 d . . . H19A H 0.7100 -0.1010 0.0378 0.044 Uiso 1 1 calc R . . H19B H 0.5732 -0.0783 -0.0107 0.044 Uiso 1 1 calc R . . C1A C 0.9372(3) -0.02729(16) 0.31739(16) 0.0393(8) Uani 1 1 d . . . H1AA H 0.8997 0.0069 0.3404 0.047 Uiso 1 1 calc R . . C20 C 1.0455(4) -0.06476(18) 0.34970(17) 0.0456(9) Uani 1 1 d . . . C21 C 1.1005(4) -0.11322(17) 0.3146(2) 0.0479(9) Uani 1 1 d . . . H21 H 1.1738 -0.1393 0.3361 0.057 Uiso 1 1 calc R . . C22 C 1.0518(3) -0.12491(16) 0.24887(19) 0.0431(8) Uani 1 1 d . . . C23 C 0.9415(3) -0.08761(15) 0.21812(17) 0.0370(7) Uani 1 1 d . . . H23 H 0.9059 -0.0956 0.1734 0.044 Uiso 1 1 calc R . . C24 C 0.8830(3) -0.03900(15) 0.25204(15) 0.0326(7) Uani 1 1 d . . . C25 C 1.1028(5) -0.0508(2) 0.4208(2) 0.0752(14) Uani 1 1 d . . . H25A H 1.1622 -0.0126 0.4225 0.113 Uiso 1 1 calc R . . H25B H 1.1608 -0.0866 0.4390 0.113 Uiso 1 1 calc R . . H25C H 1.0225 -0.0442 0.4469 0.113 Uiso 1 1 calc R . . C26 C 1.1191(5) -0.17639(19) 0.2107(3) 0.0692(13) Uani 1 1 d . . . H26A H 1.2020 -0.1592 0.1915 0.104 Uiso 1 1 calc R . . H26B H 1.0485 -0.1921 0.1754 0.104 Uiso 1 1 calc R . . H26C H 1.1503 -0.2113 0.2407 0.104 Uiso 1 1 calc R . . C27 C 0.4998(3) 0.02129(15) 0.20690(15) 0.0341(7) Uani 1 1 d . . . H27A H 0.5008 0.0277 0.1588 0.041 Uiso 1 1 calc R . . H27B H 0.5123 0.0631 0.2287 0.041 Uiso 1 1 calc R . . C28 C 0.3554(3) -0.00667(18) 0.21981(18) 0.0463(9) Uani 1 1 d . A . H28A H 0.3301 -0.0412 0.1878 0.056 Uiso 1 1 calc R . . H28B H 0.3649 -0.0253 0.2647 0.056 Uiso 1 1 calc R . . C29 C 0.2361(5) 0.0408(3) 0.2144(3) 0.0926(17) Uani 1 1 d D . . H29A H 0.2415 0.0665 0.1741 0.111 Uiso 0.746(6) 1 calc PR A 1 H29B H 0.1435 0.0179 0.2091 0.111 Uiso 0.746(6) 1 calc PR A 1 H29C H 0.1703 0.0239 0.1771 0.111 Uiso 0.254(6) 1 calc PR A 2 H29D H 0.1883 0.0315 0.2542 0.111 Uiso 0.254(6) 1 calc PR A 2 C30 C 0.2383(5) 0.0825(3) 0.2700(3) 0.0585(14) Uani 0.746(6) 1 d PD A 1 H30A H 0.3339 0.1025 0.2787 0.070 Uiso 0.746(6) 1 calc PR A 1 H30B H 0.2201 0.0581 0.3096 0.070 Uiso 0.746(6) 1 calc PR A 1 C31 C 0.1172(6) 0.1366(3) 0.2554(3) 0.0982(19) Uani 1 1 d D . . H31A H 0.1258 0.1590 0.2134 0.118 Uiso 0.746(6) 1 calc PR A 1 H31B H 0.0191 0.1192 0.2549 0.118 Uiso 0.746(6) 1 calc PR A 1 H31C H 0.0500 0.1624 0.2254 0.118 Uiso 0.254(6) 1 calc PR A 2 H31D H 0.0585 0.1024 0.2719 0.118 Uiso 0.254(6) 1 calc PR A 2 C32 C 0.1216(5) 0.1565(2) 0.3699(4) 0.0807(16) Uani 1 1 d . . . C33 C 0.1961(6) 0.1931(2) 0.4276(4) 0.100(2) Uani 1 1 d . A . H33 H 0.1834 0.2394 0.4184 0.120 Uiso 1 1 calc R . . C34 C 0.1386(7) 0.1784(4) 0.4916(4) 0.129(3) Uani 1 1 d . . . H34A H 0.0358 0.1881 0.4877 0.193 Uiso 1 1 calc R A . H34B H 0.1889 0.2042 0.5269 0.193 Uiso 1 1 calc R . . H34C H 0.1534 0.1335 0.5021 0.193 Uiso 1 1 calc R . . C35 C 0.3541(6) 0.1775(4) 0.4319(3) 0.148(3) Uani 1 1 d . . . H35A H 0.3670 0.1315 0.4348 0.222 Uiso 1 1 calc R A . H35B H 0.4046 0.1975 0.4713 0.222 Uiso 1 1 calc R . . H35C H 0.3932 0.1934 0.3924 0.222 Uiso 1 1 calc R . . C30A C 0.2170(15) 0.1017(7) 0.2078(7) 0.0585(14) Uani 0.254(6) 1 d PD A 2 H30C H 0.1761 0.1099 0.1616 0.070 Uiso 0.254(6) 1 calc PR A 2 H30D H 0.3125 0.1221 0.2140 0.070 Uiso 0.254(6) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0544(6) 0.0437(6) 0.0693(7) -0.0123(5) 0.0008(5) -0.0015(5) F1 0.189(4) 0.073(2) 0.081(2) -0.0238(16) -0.016(2) -0.025(2) F2 0.0678(19) 0.119(3) 0.214(4) -0.056(3) 0.038(2) -0.0076(18) F3 0.127(2) 0.0469(15) 0.112(2) -0.0015(15) -0.0253(19) -0.0077(15) F4 0.166(3) 0.078(2) 0.0693(19) -0.0135(15) -0.0178(19) 0.019(2) F5 0.0574(18) 0.145(3) 0.211(4) 0.054(3) 0.025(2) 0.0019(19) F6 0.149(3) 0.0461(15) 0.0847(19) -0.0096(13) 0.0277(18) -0.0027(15) O1 0.0531(14) 0.0288(12) 0.0383(13) 0.0022(10) -0.0014(10) -0.0097(10) O2 0.0533(14) 0.0397(14) 0.0473(14) -0.0085(11) -0.0003(11) 0.0013(11) O3 0.0614(15) 0.0547(16) 0.0345(13) -0.0086(12) -0.0066(11) -0.0041(13) O4 0.0602(15) 0.0561(16) 0.0284(12) 0.0037(11) 0.0136(11) 0.0099(12) O5 0.0515(14) 0.0426(14) 0.0363(13) 0.0097(11) 0.0066(10) 0.0039(11) O6 0.0437(12) 0.0279(11) 0.0327(12) 0.0026(9) -0.0026(9) -0.0070(9) O7 0.0452(12) 0.0296(12) 0.0302(11) 0.0014(9) 0.0031(9) -0.0063(9) O8 0.086(2) 0.0444(19) 0.139(4) 0.007(2) -0.024(2) 0.0107(17) O9 0.073(2) 0.101(3) 0.158(4) -0.059(3) 0.049(2) -0.033(2) N1 0.0342(13) 0.0298(14) 0.0267(13) 0.0028(11) 0.0010(10) 0.0006(11) C1 0.0355(17) 0.0413(19) 0.0272(16) 0.0069(14) -0.0026(13) -0.0044(14) C2 0.0429(19) 0.056(2) 0.0306(17) 0.0024(16) 0.0004(14) -0.0050(17) C3 0.0322(16) 0.0361(18) 0.0366(18) 0.0083(14) -0.0009(13) -0.0036(14) C4 0.048(2) 0.081(3) 0.038(2) 0.006(2) 0.0078(16) -0.011(2) C5 0.049(2) 0.083(3) 0.045(2) 0.018(2) 0.0022(17) -0.023(2) C6 0.052(2) 0.052(2) 0.048(2) 0.0124(18) -0.0089(17) -0.0198(18) C7 0.0401(18) 0.044(2) 0.0298(17) 0.0094(15) -0.0044(14) -0.0061(15) C8 0.066(2) 0.0315(19) 0.051(2) 0.0046(17) -0.0095(18) -0.0088(17) C9 0.063(2) 0.0266(18) 0.063(2) 0.0002(17) -0.0105(19) 0.0015(16) C10 0.052(2) 0.037(2) 0.070(3) -0.0173(19) 0.0109(19) -0.0099(17) C11 0.053(2) 0.063(3) 0.051(2) -0.022(2) -0.0012(17) -0.011(2) C12 0.073(3) 0.078(3) 0.0239(18) -0.0124(19) -0.0047(17) 0.021(2) C13 0.077(3) 0.071(3) 0.0289(19) 0.0040(19) 0.0164(17) 0.020(2) C14 0.072(3) 0.068(3) 0.041(2) 0.019(2) 0.0197(19) 0.003(2) C15 0.074(3) 0.050(2) 0.043(2) 0.0169(18) 0.0082(18) 0.006(2) C16 0.054(2) 0.0286(18) 0.050(2) 0.0087(16) 0.0067(16) 0.0010(15) C17 0.050(2) 0.0286(17) 0.046(2) 0.0033(15) 0.0036(15) -0.0072(15) C18 0.0437(18) 0.0335(17) 0.0312(17) -0.0025(14) -0.0038(14) -0.0078(14) C19 0.0490(19) 0.0330(18) 0.0285(17) -0.0037(14) 0.0016(14) -0.0031(15) C1A 0.0358(17) 0.0413(19) 0.0406(19) 0.0011(15) 0.0031(14) 0.0028(14) C20 0.0403(19) 0.055(2) 0.0393(19) 0.0119(17) -0.0053(15) -0.0004(17) C21 0.0326(18) 0.045(2) 0.066(3) 0.0188(19) 0.0026(17) 0.0061(15) C22 0.0361(18) 0.0324(18) 0.063(2) 0.0068(17) 0.0174(16) -0.0013(14) C23 0.0366(17) 0.0357(18) 0.0395(18) 0.0008(15) 0.0083(14) -0.0089(14) C24 0.0284(15) 0.0342(17) 0.0351(17) 0.0081(14) 0.0031(12) -0.0038(13) C25 0.070(3) 0.098(4) 0.052(3) 0.009(2) -0.017(2) 0.011(3) C26 0.062(3) 0.044(2) 0.107(4) -0.001(2) 0.033(2) 0.009(2) C27 0.0366(17) 0.0305(16) 0.0337(17) 0.0026(14) -0.0027(13) 0.0054(13) C28 0.0368(18) 0.057(2) 0.046(2) 0.0060(18) 0.0082(15) 0.0060(16) C29 0.060(3) 0.073(3) 0.147(5) -0.014(3) 0.026(3) 0.003(2) C30 0.052(3) 0.076(4) 0.046(3) -0.005(3) -0.004(2) -0.004(3) C31 0.094(4) 0.062(3) 0.145(5) -0.027(3) 0.043(4) 0.017(3) C32 0.049(3) 0.040(3) 0.151(6) -0.005(3) 0.000(3) 0.019(2) C33 0.093(4) 0.042(3) 0.148(6) 0.012(3) -0.058(4) 0.008(3) C34 0.090(4) 0.140(6) 0.155(7) -0.076(6) 0.006(4) 0.030(4) C35 0.064(3) 0.269(10) 0.106(5) 0.077(6) -0.012(3) -0.029(5) C30A 0.052(3) 0.076(4) 0.046(3) -0.005(3) -0.004(2) -0.004(3) _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 P1 F5 1.541(3) . ? P1 F2 1.574(3) . ? P1 F4 1.578(3) . ? P1 F1 1.579(3) . ? P1 F6 1.586(3) . ? P1 F3 1.588(3) . ? O1 C7 1.380(4) . ? O1 C8 1.430(4) . ? O2 C9 1.422(4) . ? O2 C10 1.423(4) . ? O3 C12 1.425(4) . ? O3 C11 1.425(5) . ? O4 C13 1.424(4) . ? O4 C14 1.428(5) . ? O5 C16 1.413(4) . ? O5 C15 1.428(4) . ? O6 C17 1.424(4) . ? O6 C18 1.442(4) . ? O7 C1 1.378(4) . ? O7 C19 1.440(4) . ? O8 C32 1.324(7) . ? O8 C31 1.446(7) . ? O9 C32 1.198(6) . ? N1 C3 1.492(4) . ? N1 C27 1.495(4) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? C1 C2 1.388(5) . ? C1 C7 1.406(5) . ? C2 C4 1.391(5) . ? C2 H2 0.9500 . ? C3 C24 1.509(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.368(6) . ? C4 H4 0.9500 . ? C5 C6 1.389(6) . ? C5 H5 0.9500 . ? C6 C7 1.388(5) . ? C6 H6 0.9500 . ? C8 C9 1.493(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.494(6) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.481(6) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.491(6) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.495(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.490(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C1A C24 1.393(4) . ? C1A C20 1.394(5) . ? C1A H1AA 0.9500 . ? C20 C21 1.382(5) . ? C20 C25 1.516(5) . ? C21 C22 1.387(5) . ? C21 H21 0.9500 . ? C22 C23 1.393(5) . ? C22 C26 1.515(5) . ? C23 C24 1.386(4) . ? C23 H23 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 C28 1.528(4) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.498(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30A 1.305(13) . ? C29 C30 1.433(7) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C29 H29C 0.9900 . ? C29 H29D 0.9900 . ? C30 C31 1.616(7) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C30A 1.602(13) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C31 H31C 0.9900 . ? C31 H31D 0.9900 . ? C32 C33 1.513(8) . ? C33 C34 1.498(9) . ? C33 C35 1.513(8) . ? C33 H33 1.0000 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C30A H30C 0.9900 . ? C30A H30D 0.9900 . ? 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 F5 P1 F2 178.2(2) . . ? F5 P1 F4 91.1(2) . . ? F2 P1 F4 89.2(2) . . ? F5 P1 F1 90.7(2) . . ? F2 P1 F1 89.0(2) . . ? F4 P1 F1 177.3(2) . . ? F5 P1 F6 89.02(19) . . ? F2 P1 F6 89.3(2) . . ? F4 P1 F6 88.87(16) . . ? F1 P1 F6 89.13(17) . . ? F5 P1 F3 92.3(2) . . ? F2 P1 F3 89.4(2) . . ? F4 P1 F3 90.53(17) . . ? F1 P1 F3 91.42(17) . . ? F6 P1 F3 178.53(18) . . ? C7 O1 C8 115.9(3) . . ? C9 O2 C10 112.1(3) . . ? C12 O3 C11 111.9(3) . . ? C13 O4 C14 112.1(3) . . ? C16 O5 C15 111.5(3) . . ? C17 O6 C18 111.6(2) . . ? C1 O7 C19 115.3(2) . . ? C32 O8 C31 117.2(4) . . ? C3 N1 C27 114.3(2) . . ? C3 N1 H1A 108.7 . . ? C27 N1 H1A 108.7 . . ? C3 N1 H1B 108.7 . . ? C27 N1 H1B 108.7 . . ? H1A N1 H1B 107.6 . . ? O7 C1 C2 123.9(3) . . ? O7 C1 C7 116.6(3) . . ? C2 C1 C7 119.6(3) . . ? C1 C2 C4 120.3(4) . . ? C1 C2 H2 119.9 . . ? C4 C2 H2 119.9 . . ? N1 C3 C24 110.7(2) . . ? N1 C3 H3A 109.5 . . ? C24 C3 H3A 109.5 . . ? N1 C3 H3B 109.5 . . ? C24 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C2 120.1(4) . . ? C5 C4 H4 119.9 . . ? C2 C4 H4 119.9 . . ? C4 C5 C6 120.5(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C7 C6 C5 120.3(4) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? O1 C7 C6 124.1(3) . . ? O1 C7 C1 116.6(3) . . ? C6 C7 C1 119.3(3) . . ? O1 C8 C9 110.1(3) . . ? O1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? O1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? O2 C9 C8 110.2(3) . . ? O2 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? O2 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O2 C10 C11 110.6(3) . . ? O2 C10 H10A 109.5 . . ? C11 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? C11 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O3 C11 C10 109.2(3) . . ? O3 C11 H11A 109.8 . . ? C10 C11 H11A 109.8 . . ? O3 C11 H11B 109.8 . . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? O3 C12 C13 109.3(3) . . ? O3 C12 H12A 109.8 . . ? C13 C12 H12A 109.8 . . ? O3 C12 H12B 109.8 . . ? C13 C12 H12B 109.8 . . ? H12A C12 H12B 108.3 . . ? O4 C13 C12 111.0(3) . . ? O4 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? O4 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? O4 C14 C15 109.5(3) . . ? O4 C14 H14A 109.8 . . ? C15 C14 H14A 109.8 . . ? O4 C14 H14B 109.8 . . ? C15 C14 H14B 109.8 . . ? H14A C14 H14B 108.2 . . ? O5 C15 C14 108.9(3) . . ? O5 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? O5 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? O5 C16 C17 108.4(3) . . ? O5 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? O5 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.4 . . ? O6 C17 C16 109.0(3) . . ? O6 C17 H17A 109.9 . . ? C16 C17 H17A 109.9 . . ? O6 C17 H17B 109.9 . . ? C16 C17 H17B 109.9 . . ? H17A C17 H17B 108.3 . . ? O6 C18 C19 110.6(2) . . ? O6 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? O6 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? O7 C19 C18 110.1(3) . . ? O7 C19 H19A 109.6 . . ? C18 C19 H19A 109.6 . . ? O7 C19 H19B 109.6 . . ? C18 C19 H19B 109.6 . . ? H19A C19 H19B 108.2 . . ? C24 C1A C20 121.3(3) . . ? C24 C1A H1AA 119.4 . . ? C20 C1A H1AA 119.4 . . ? C21 C20 C1A 118.1(3) . . ? C21 C20 C25 121.7(3) . . ? C1A C20 C25 120.1(4) . . ? C20 C21 C22 122.0(3) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C23 118.7(3) . . ? C21 C22 C26 120.8(3) . . ? C23 C22 C26 120.5(4) . . ? C24 C23 C22 120.8(3) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C1A 119.1(3) . . ? C23 C24 C3 121.6(3) . . ? C1A C24 C3 119.3(3) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N1 C27 C28 111.7(3) . . ? N1 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? N1 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 113.5(3) . . ? C29 C28 H28A 108.9 . . ? C27 C28 H28A 108.9 . . ? C29 C28 H28B 108.9 . . ? C27 C28 H28B 108.9 . . ? H28A C28 H28B 107.7 . . ? C30A C29 C30 57.6(7) . . ? C30A C29 C28 139.6(8) . . ? C30 C29 C28 114.2(5) . . ? C30A C29 H29A 52.6 . . ? C30 C29 H29A 108.7 . . ? C28 C29 H29A 108.7 . . ? C30A C29 H29B 111.2 . . ? C30 C29 H29B 108.7 . . ? C28 C29 H29B 108.7 . . ? H29A C29 H29B 107.6 . . ? C30A C29 H29C 102.2 . . ? C30 C29 H29C 141.3 . . ? C28 C29 H29C 102.2 . . ? H29A C29 H29C 69.4 . . ? H29B C29 H29C 43.6 . . ? C30A C29 H29D 102.2 . . ? C30 C29 H29D 56.1 . . ? C28 C29 H29D 102.2 . . ? H29A C29 H29D 149.1 . . ? H29B C29 H29D 61.3 . . ? H29C C29 H29D 104.8 . . ? C29 C30 C31 110.1(4) . . ? C29 C30 H30A 109.7 . . ? C31 C30 H30A 109.7 . . ? C29 C30 H30B 109.7 . . ? C31 C30 H30B 109.7 . . ? H30A C30 H30B 108.2 . . ? O8 C31 C30A 130.0(7) . . ? O8 C31 C30 99.2(4) . . ? C30A C31 C30 48.6(6) . . ? O8 C31 H31A 111.9 . . ? C30A C31 H31A 65.6 . . ? C30 C31 H31A 111.9 . . ? O8 C31 H31B 111.9 . . ? C30A C31 H31B 115.5 . . ? C30 C31 H31B 111.9 . . ? H31A C31 H31B 109.6 . . ? O8 C31 H31C 104.8 . . ? C30A C31 H31C 104.8 . . ? C30 C31 H31C 152.7 . . ? H31A C31 H31C 46.5 . . ? H31B C31 H31C 70.8 . . ? O8 C31 H31D 104.8 . . ? C30A C31 H31D 104.8 . . ? C30 C31 H31D 80.1 . . ? H31A C31 H31D 138.2 . . ? H31B C31 H31D 35.0 . . ? H31C C31 H31D 105.8 . . ? O9 C32 O8 123.7(6) . . ? O9 C32 C33 123.4(7) . . ? O8 C32 C33 112.9(5) . . ? C34 C33 C32 113.0(5) . . ? C34 C33 C35 110.6(5) . . ? C32 C33 C35 107.3(6) . . ? C34 C33 H33 108.6 . . ? C32 C33 H33 108.6 . . ? C35 C33 H33 108.6 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C29 C30A C31 118.3(11) . . ? C29 C30A H30C 107.7 . . ? C31 C30A H30C 107.7 . . ? C29 C30A H30D 107.7 . . ? C31 C30A H30D 107.7 . . ? H30C C30A H30D 107.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.690 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.056