# Electronic Supplementary Material (ESI) for Chemical Communications # 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_shelx _database_code_depnum_ccdc_archive 'CCDC 910542' #TrackingRef '0203.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H40 F6 N2 O3 S' _chemical_formula_weight 550.64 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.940(19) _cell_length_b 16.839(11) _cell_length_c 29.83(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.479(11) _cell_angle_gamma 90.00 _cell_volume 11337(14) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 10822 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 31.4 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.290 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4672 _exptl_absorpt_coefficient_mu 0.180 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9614 _exptl_absorpt_correction_T_max 0.9857 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21196 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0839 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.03 _reflns_number_total 8728 _reflns_number_gt 6416 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. The terminal carbon of one of the TBA arms is modelled as disordered over 2 possible positions. Distance and thermal parameter restraints were applied. ; _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^)+(0.0159P)^2^+120.0448P] 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 8728 _refine_ls_number_parameters 669 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1590 _refine_ls_R_factor_gt 0.1274 _refine_ls_wR_factor_ref 0.2321 _refine_ls_wR_factor_gt 0.2168 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.145 _refine_ls_shift/su_max 0.002 _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 S1 S -0.03547(8) 0.41570(11) 0.31579(6) 0.0379(4) Uani 1 1 d . . . F1 F 0.2596(2) 0.3448(3) 0.3705(2) 0.0773(16) Uani 1 1 d . . . F2 F 0.2588(2) 0.4653(3) 0.3928(2) 0.0879(18) Uani 1 1 d . . . F3 F 0.2895(2) 0.3733(4) 0.4440(2) 0.0887(18) Uani 1 1 d . . . F4 F 0.1153(3) 0.3950(3) 0.51914(18) 0.094(2) Uani 1 1 d . . . F5 F 0.1454(2) 0.2761(3) 0.51488(18) 0.0819(17) Uani 1 1 d . . . F6 F 0.0535(2) 0.3055(3) 0.48368(16) 0.0662(14) Uani 1 1 d . . . O1 O -0.0330(2) 0.4840(3) 0.34625(17) 0.0439(12) Uani 1 1 d . . . O2 O -0.0636(2) 0.4323(3) 0.26509(16) 0.0455(13) Uani 1 1 d . . . O3 O -0.0572(2) 0.3440(3) 0.33215(16) 0.0395(12) Uani 1 1 d . . . N6 N 0.0344(2) 0.3947(3) 0.31902(19) 0.0374(14) Uani 1 1 d . . . H6 H 0.0419 0.3909 0.2929 0.045 Uiso 1 1 calc R . . C1 C 0.2484(4) 0.3901(6) 0.4035(3) 0.063(2) Uani 1 1 d . . . C2 C 0.0808(3) 0.3829(4) 0.3615(2) 0.0361(16) Uani 1 1 d . . . C3 C 0.1858(3) 0.3792(5) 0.4035(3) 0.048(2) Uani 1 1 d . . . C4 C 0.0710(3) 0.3626(4) 0.4041(2) 0.0399(17) Uani 1 1 d . . . H4 H 0.0326 0.3560 0.4045 0.048 Uiso 1 1 calc R . . C5 C 0.1087(4) 0.3331(5) 0.4897(3) 0.057(2) Uani 1 1 d . . . C6 C 0.1387(3) 0.3910(4) 0.3621(3) 0.0396(17) Uani 1 1 d . . . H6A H 0.1459 0.4045 0.3342 0.048 Uiso 1 1 calc R . . C7 C 0.1182(3) 0.3526(4) 0.4446(2) 0.0415(18) Uani 1 1 d . . . C8 C 0.1768(3) 0.3591(4) 0.4458(3) 0.0470(19) Uani 1 1 d . . . H8 H 0.2084 0.3503 0.4736 0.056 Uiso 1 1 calc R . . S2 S 0.39724(8) 0.41148(12) 0.20497(7) 0.0418(5) Uani 1 1 d . . . F16 F 0.5539(3) 0.4625(4) 0.0425(2) 0.0948(19) Uani 1 1 d . . . F17 F 0.5636(3) 0.3370(3) 0.0426(2) 0.0924(19) Uani 1 1 d . . . F18 F 0.6039(2) 0.4034(4) 0.10592(17) 0.0787(16) Uani 1 1 d . . . F101 F 0.2921(3) 0.3390(5) 0.0312(2) 0.124(3) Uani 1 1 d . . . F102 F 0.3376(3) 0.2943(4) -0.0116(2) 0.103(2) Uani 1 1 d . . . F103 F 0.3192(3) 0.4173(4) -0.0112(3) 0.150(4) Uani 1 1 d . . . O4 O 0.3696(2) 0.4834(3) 0.18061(16) 0.0434(12) Uani 1 1 d . . . O5 O 0.3581(2) 0.3427(3) 0.19225(18) 0.0498(14) Uani 1 1 d . . . O6 O 0.4276(2) 0.4227(3) 0.25617(16) 0.0438(12) Uani 1 1 d . . . N7 N 0.4542(2) 0.3905(3) 0.1859(2) 0.0431(15) Uani 1 1 d . . . H7 H 0.4884 0.3827 0.2070 0.052 Uiso 1 1 calc R . . C39 C 0.3959(3) 0.3715(4) 0.1023(3) 0.0464(19) Uani 1 1 d . . . H39 H 0.3612 0.3658 0.1095 0.056 Uiso 1 1 calc R . . C40 C 0.4498(3) 0.3848(4) 0.1385(2) 0.0413(18) Uani 1 1 d . . . C41 C 0.4991(4) 0.3876(5) 0.0802(3) 0.052(2) Uani 1 1 d . . . C42 C 0.5544(4) 0.3965(6) 0.0683(3) 0.064(2) Uani 1 1 d . . . C100 C 0.3365(4) 0.3545(7) 0.0165(3) 0.075(3) Uani 1 1 d . . . C102 C 0.3947(4) 0.3669(5) 0.0551(3) 0.062(3) Uani 1 1 d . . . C103 C 0.5019(3) 0.3930(4) 0.1267(3) 0.0461(19) Uani 1 1 d . . . H103 H 0.5381 0.4021 0.1504 0.055 Uiso 1 1 calc R . . C105 C 0.4459(4) 0.3758(5) 0.0438(3) 0.064(3) Uani 1 1 d . . . H105 H 0.4446 0.3738 0.0124 0.077 Uiso 1 1 calc R . . N99 N 0.0000 0.1647(5) 0.2500 0.041(2) Uani 1 2 d S . . C401 C -0.0330(4) 0.0914(5) 0.1204(3) 0.064(2) Uani 1 1 d . . . H40A H 0.0040 0.0626 0.1276 0.077 Uiso 1 1 calc R . . H40B H -0.0636 0.0536 0.1203 0.077 Uiso 1 1 calc R . . C402 C -0.0271(4) 0.1536(5) 0.1596(3) 0.050(2) Uani 1 1 d . . . H40C H 0.0038 0.1914 0.1604 0.060 Uiso 1 1 calc R . . H40D H -0.0641 0.1823 0.1532 0.060 Uiso 1 1 calc R . . C403 C -0.0118(4) 0.1107(4) 0.2066(3) 0.047(2) Uani 1 1 d . . . H40E H 0.0231 0.0784 0.2107 0.056 Uiso 1 1 calc R . . H40F H -0.0441 0.0751 0.2054 0.056 Uiso 1 1 calc R . . C404 C 0.0525(3) 0.2192(4) 0.2554(3) 0.0445(19) Uani 1 1 d . . . H40G H 0.0586 0.2519 0.2834 0.053 Uiso 1 1 calc R . . H40H H 0.0424 0.2545 0.2281 0.053 Uiso 1 1 calc R . . C405 C 0.1108(3) 0.1778(5) 0.2597(3) 0.057(2) Uani 1 1 d . . . H40I H 0.1071 0.1488 0.2308 0.069 Uiso 1 1 calc R . . H40J H 0.1212 0.1404 0.2860 0.069 Uiso 1 1 calc R . . C406 C 0.1589(3) 0.2427(5) 0.2685(3) 0.065(3) Uani 1 1 d . . . H40K H 0.1468 0.2815 0.2430 0.079 Uiso 1 1 calc R . . H40L H 0.1632 0.2698 0.2981 0.079 Uiso 1 1 calc R . . C502 C 0.2186(4) 0.2070(7) 0.2707(4) 0.086(3) Uani 1 1 d . . . H50A H 0.2313 0.1696 0.2964 0.129 Uiso 1 1 calc R . . H50B H 0.2475 0.2486 0.2759 0.129 Uiso 1 1 calc R . . H50C H 0.2146 0.1805 0.2413 0.129 Uiso 1 1 calc R . . C503 C -0.0483(5) 0.1284(6) 0.0714(3) 0.083(3) Uani 1 1 d . . . H50D H -0.0844 0.1581 0.0644 0.124 Uiso 1 1 calc R . . H50E H -0.0533 0.0872 0.0481 0.124 Uiso 1 1 calc R . . H50F H -0.0168 0.1631 0.0706 0.124 Uiso 1 1 calc R . . N4 N 0.1880(3) 0.4058(4) 0.1182(2) 0.0434(15) Uani 1 1 d . A . C99 C 0.0549(4) 0.4163(7) 0.0003(4) 0.093(4) Uani 1 1 d . . . H99A H 0.0285 0.3880 0.0134 0.112 Uiso 1 1 calc R . . H99B H 0.0467 0.4726 0.0013 0.112 Uiso 1 1 calc R . . C25 C 0.0415(4) 0.3915(8) -0.0508(4) 0.111(4) Uani 1 1 d . . . H25A H 0.0703 0.4144 -0.0630 0.167 Uiso 1 1 calc R . . H25B H 0.0026 0.4098 -0.0694 0.167 Uiso 1 1 calc R . . H25C H 0.0429 0.3347 -0.0527 0.167 Uiso 1 1 calc R . . C121 C 0.2787(3) 0.5712(4) 0.0841(3) 0.055(2) Uani 1 1 d . . . H12A H 0.2632 0.5589 0.0505 0.066 Uiso 1 1 calc R . . H12B H 0.3168 0.5450 0.0972 0.066 Uiso 1 1 calc R . . C122 C 0.1280(3) 0.4233(5) 0.0820(3) 0.049(2) Uani 1 1 d . . . H12C H 0.0983 0.3964 0.0919 0.059 Uiso 1 1 calc R . . H12D H 0.1208 0.4799 0.0827 0.059 Uiso 1 1 calc R . . C123 C 0.2371(3) 0.5385(5) 0.1079(3) 0.054(2) Uani 1 1 d . . . H12E H 0.2494 0.5560 0.1407 0.065 Uiso 1 1 calc R . . H12F H 0.1974 0.5582 0.0918 0.065 Uiso 1 1 calc R . . C124 C 0.1565(4) 0.2618(5) 0.1246(3) 0.057(2) Uani 1 1 d . . . H12G H 0.1207 0.2662 0.0972 0.069 Uiso 1 1 calc R . . H12H H 0.1469 0.2758 0.1528 0.069 Uiso 1 1 calc R . . C125 C 0.1190(3) 0.4006(5) 0.0320(3) 0.062(2) Uani 1 1 d . . . H12I H 0.1280 0.3447 0.0306 0.074 Uiso 1 1 calc R . . H12J H 0.1457 0.4308 0.0203 0.074 Uiso 1 1 calc R . . C126 C 0.2371(3) 0.4491(4) 0.1061(3) 0.0420(18) Uani 1 1 d . . . H12K H 0.2749 0.4306 0.1277 0.050 Uiso 1 1 calc R . . H12L H 0.2351 0.4334 0.0743 0.050 Uiso 1 1 calc R . . C127 C 0.2028(3) 0.3177(4) 0.1191(3) 0.0423(18) Uani 1 1 d . . . H12M H 0.2099 0.3046 0.0898 0.051 Uiso 1 1 calc R . . H12N H 0.2395 0.3084 0.1451 0.051 Uiso 1 1 calc R . . C128 C 0.2315(5) 0.4552(8) 0.2530(4) 0.105(4) Uani 1 1 d D . . H12O H 0.2091 0.5044 0.2461 0.126 Uiso 0.664(18) 1 calc PR A 1 H12P H 0.2086 0.4166 0.2637 0.126 Uiso 0.664(18) 1 calc PR A 1 H12Q H 0.2041 0.4179 0.2592 0.126 Uiso 0.336(18) 1 d PR A 2 H12R H 0.2692 0.4467 0.2779 0.126 Uiso 0.336(18) 1 d PR A 2 C99A C 0.2893(8) 0.4692(11) 0.2916(5) 0.129(10) Uani 0.664(18) 1 d PD A 1 H99C H 0.3177 0.4890 0.2780 0.193 Uiso 0.664(18) 1 calc PR A 1 H99D H 0.3034 0.4201 0.3079 0.193 Uiso 0.664(18) 1 calc PR A 1 H99E H 0.2839 0.5073 0.3137 0.193 Uiso 0.664(18) 1 calc PR A 1 C99B C 0.2120(11) 0.5326(12) 0.2629(10) 0.067(10) Uani 0.336(18) 1 d PD A 2 H99F H 0.2059 0.5314 0.2931 0.101 Uiso 0.336(18) 1 calc PR A 2 H99G H 0.1755 0.5462 0.2385 0.101 Uiso 0.336(18) 1 calc PR A 2 H99H H 0.2416 0.5715 0.2637 0.101 Uiso 0.336(18) 1 calc PR A 2 C130 C 0.1846(4) 0.4331(5) 0.1662(3) 0.055(2) Uani 1 1 d . . . H13A H 0.1725 0.4884 0.1634 0.065 Uiso 1 1 calc R A . H13B H 0.1537 0.4028 0.1728 0.065 Uiso 1 1 calc R . . C131 C 0.2405(4) 0.4253(5) 0.2083(3) 0.057(2) Uani 1 1 d . A . H13C H 0.2525 0.3700 0.2125 0.068 Uiso 1 1 calc R . . H13D H 0.2719 0.4554 0.2025 0.068 Uiso 1 1 calc R . . C132 C 0.2881(4) 0.6619(5) 0.0902(3) 0.070(3) Uani 1 1 d . . . H13E H 0.2505 0.6884 0.0783 0.104 Uiso 1 1 calc R . . H13F H 0.3131 0.6795 0.0728 0.104 Uiso 1 1 calc R . . H13G H 0.3065 0.6743 0.1233 0.104 Uiso 1 1 calc R . . C137 C 0.1798(5) 0.1758(5) 0.1291(3) 0.071(3) Uani 1 1 d . . . H13W H 0.1950 0.1648 0.1034 0.086 Uiso 1 1 calc R . . H13X H 0.2122 0.1699 0.1589 0.086 Uiso 1 1 calc R . . C504 C 0.1308(6) 0.1156(6) 0.1274(5) 0.115(5) Uani 1 1 d . . . H50G H 0.1163 0.1256 0.1532 0.172 Uiso 1 1 calc R . . H50H H 0.1466 0.0627 0.1301 0.172 Uiso 1 1 calc R . . H50I H 0.0989 0.1208 0.0977 0.172 Uiso 1 1 calc R . . N3 N 0.5000 0.1626(5) 0.2500 0.058(3) Uani 1 2 d S . . C148 C 0.4269(4) 0.1715(5) 0.2970(4) 0.068(3) Uani 1 1 d . . . H14A H 0.3930 0.1486 0.2727 0.081 Uiso 1 1 calc R . . H14B H 0.4497 0.1283 0.3160 0.081 Uiso 1 1 calc R . . C149 C 0.4654(4) 0.2156(5) 0.2730(3) 0.059(2) Uani 1 1 d . . . H14C H 0.4401 0.2504 0.2488 0.071 Uiso 1 1 calc R . . H14D H 0.4933 0.2488 0.2966 0.071 Uiso 1 1 calc R . . C150 C 0.3676(4) 0.0963(5) 0.1394(3) 0.070(3) Uani 1 1 d . . . H15A H 0.3451 0.0730 0.1578 0.085 Uiso 1 1 calc R . . H15B H 0.3873 0.0536 0.1287 0.085 Uiso 1 1 calc R . . C151 C 0.4572(3) 0.1093(5) 0.2130(3) 0.057(2) Uani 1 1 d . . . H15C H 0.4800 0.0723 0.2010 0.069 Uiso 1 1 calc R . . H15D H 0.4345 0.0784 0.2283 0.069 Uiso 1 1 calc R . . C152 C 0.3712(4) 0.1828(6) 0.3552(3) 0.077(3) Uani 1 1 d . . . H15X H 0.3356 0.1606 0.3332 0.116 Uiso 1 1 calc R . . H15Y H 0.3611 0.2200 0.3756 0.116 Uiso 1 1 calc R . . H15Z H 0.3950 0.1410 0.3740 0.116 Uiso 1 1 calc R . . C153 C 0.3251(4) 0.1402(6) 0.0959(4) 0.082(3) Uani 1 1 d . . . H15R H 0.3045 0.1811 0.1064 0.123 Uiso 1 1 calc R . . H15I H 0.2970 0.1032 0.0762 0.123 Uiso 1 1 calc R . . H15J H 0.3474 0.1635 0.0778 0.123 Uiso 1 1 calc R . . C155 C 0.4055(4) 0.2247(5) 0.3280(4) 0.079(3) Uani 1 1 d . . . H15E H 0.3806 0.2656 0.3084 0.094 Uiso 1 1 calc R . . H15F H 0.4395 0.2508 0.3506 0.094 Uiso 1 1 calc R . . C156 C 0.4142(4) 0.1534(5) 0.1710(3) 0.068(3) Uani 1 1 d . . . H15G H 0.4359 0.1779 0.1524 0.081 Uiso 1 1 calc R . . H15H H 0.3946 0.1951 0.1826 0.081 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 S1 0.0303(10) 0.0371(11) 0.0425(10) -0.0029(8) 0.0071(7) 0.0016(9) F1 0.048(3) 0.090(4) 0.103(4) -0.009(3) 0.037(3) 0.005(3) F2 0.043(3) 0.067(4) 0.156(6) 0.017(4) 0.037(3) -0.008(3) F3 0.035(3) 0.130(5) 0.087(4) 0.012(3) 0.002(3) 0.009(3) F4 0.156(6) 0.082(4) 0.054(3) -0.025(3) 0.046(4) -0.026(4) F5 0.068(4) 0.103(4) 0.066(3) 0.033(3) 0.012(3) 0.018(3) F6 0.068(3) 0.083(4) 0.052(3) 0.009(2) 0.027(2) 0.007(3) O1 0.036(3) 0.040(3) 0.052(3) -0.008(2) 0.011(2) -0.001(2) O2 0.030(3) 0.058(4) 0.042(3) 0.003(2) 0.003(2) 0.009(3) O3 0.036(3) 0.027(3) 0.053(3) -0.002(2) 0.011(2) -0.008(2) N6 0.022(3) 0.047(4) 0.041(3) 0.000(3) 0.008(2) 0.003(3) C1 0.035(5) 0.078(7) 0.069(6) 0.004(5) 0.009(4) 0.004(5) C2 0.025(4) 0.032(4) 0.046(4) 0.003(3) 0.005(3) 0.005(3) C3 0.024(4) 0.047(5) 0.065(5) 0.003(4) 0.003(3) 0.004(4) C4 0.027(4) 0.035(4) 0.054(5) -0.008(3) 0.010(3) -0.003(3) C5 0.051(5) 0.052(6) 0.055(5) -0.001(4) 0.000(4) -0.002(5) C6 0.032(4) 0.038(5) 0.051(4) 0.004(3) 0.016(3) 0.006(4) C7 0.041(5) 0.041(5) 0.037(4) 0.000(3) 0.007(3) 0.001(4) C8 0.034(4) 0.049(5) 0.046(5) -0.002(3) -0.004(3) 0.002(4) S2 0.0310(10) 0.0374(12) 0.0474(11) -0.0005(8) 0.0003(8) 0.0026(9) F16 0.105(5) 0.093(4) 0.092(4) 0.025(3) 0.040(4) 0.024(4) F17 0.099(5) 0.094(4) 0.099(4) -0.036(3) 0.052(4) 0.004(4) F18 0.058(3) 0.122(5) 0.058(3) 0.009(3) 0.021(3) 0.012(3) F101 0.054(4) 0.218(8) 0.071(4) -0.048(5) -0.016(3) 0.009(5) F102 0.086(4) 0.118(5) 0.078(4) -0.052(4) -0.009(3) 0.011(4) F103 0.136(6) 0.082(5) 0.135(6) 0.014(4) -0.085(5) 0.014(4) O4 0.039(3) 0.033(3) 0.050(3) 0.001(2) 0.004(2) 0.006(2) O5 0.043(3) 0.035(3) 0.060(3) -0.001(2) 0.002(3) -0.001(3) O6 0.030(3) 0.050(3) 0.041(3) -0.002(2) -0.001(2) 0.002(2) N7 0.030(3) 0.050(4) 0.042(4) 0.005(3) 0.002(3) 0.014(3) C39 0.039(4) 0.034(5) 0.055(5) -0.009(3) 0.002(4) 0.007(4) C40 0.036(4) 0.035(4) 0.042(4) 0.005(3) -0.001(3) 0.011(4) C41 0.047(5) 0.039(5) 0.061(5) -0.006(4) 0.007(4) 0.021(4) C42 0.073(7) 0.067(7) 0.047(5) 0.007(4) 0.012(5) 0.014(5) C100 0.053(6) 0.097(9) 0.056(6) -0.015(5) -0.008(5) 0.030(6) C102 0.060(6) 0.054(6) 0.044(5) -0.015(4) -0.018(4) 0.018(5) C103 0.046(5) 0.041(5) 0.042(4) -0.003(3) 0.003(3) 0.010(4) C105 0.076(7) 0.061(6) 0.042(5) -0.006(4) 0.000(4) 0.023(5) N99 0.050(6) 0.025(5) 0.051(5) 0.000 0.022(4) 0.000 C401 0.087(7) 0.063(6) 0.051(5) -0.010(4) 0.033(5) 0.006(5) C402 0.055(5) 0.047(5) 0.050(5) -0.001(4) 0.021(4) -0.002(4) C403 0.060(5) 0.035(5) 0.052(5) -0.007(3) 0.028(4) 0.002(4) C404 0.038(4) 0.043(5) 0.051(5) -0.001(3) 0.012(3) -0.008(4) C405 0.049(5) 0.057(6) 0.069(6) 0.008(4) 0.024(4) 0.002(5) C406 0.039(5) 0.075(7) 0.075(6) 0.025(5) 0.010(4) 0.001(5) C502 0.049(6) 0.118(9) 0.092(8) 0.035(6) 0.025(5) 0.009(6) C503 0.130(10) 0.070(7) 0.058(6) 0.006(5) 0.045(6) 0.004(6) N4 0.031(3) 0.042(4) 0.054(4) -0.009(3) 0.010(3) -0.002(3) C99 0.034(5) 0.135(10) 0.097(8) 0.020(7) 0.004(5) -0.009(6) C25 0.062(7) 0.179(13) 0.070(7) 0.013(8) -0.006(6) 0.026(8) C121 0.045(5) 0.039(5) 0.073(6) 0.017(4) 0.007(4) 0.009(4) C122 0.026(4) 0.045(5) 0.068(5) -0.006(4) 0.005(4) -0.001(4) C123 0.031(4) 0.056(6) 0.073(6) 0.002(4) 0.014(4) -0.006(4) C124 0.050(5) 0.053(6) 0.086(6) -0.009(4) 0.045(5) -0.013(5) C125 0.034(5) 0.061(6) 0.075(6) 0.003(4) -0.002(4) 0.003(4) C126 0.033(4) 0.044(5) 0.046(4) -0.005(3) 0.009(3) -0.009(4) C127 0.035(4) 0.037(5) 0.057(5) -0.007(3) 0.018(4) 0.000(4) C128 0.086(9) 0.160(13) 0.074(8) -0.054(8) 0.032(7) -0.016(8) C99A 0.20(3) 0.133(18) 0.056(11) -0.015(10) 0.049(14) -0.053(17) C99B 0.060(19) 0.06(2) 0.073(19) -0.005(14) 0.008(14) -0.015(15) C130 0.055(5) 0.049(5) 0.068(6) -0.009(4) 0.030(4) 0.003(4) C131 0.056(5) 0.058(6) 0.060(5) -0.005(4) 0.023(4) -0.008(5) C132 0.054(6) 0.055(6) 0.083(7) 0.014(5) 0.000(5) -0.012(5) C137 0.106(8) 0.050(6) 0.083(7) -0.014(5) 0.064(6) -0.010(6) C504 0.178(13) 0.051(7) 0.166(12) -0.027(7) 0.123(11) -0.028(8) N3 0.042(6) 0.034(6) 0.082(7) 0.000 0.000(5) 0.000 C148 0.053(6) 0.034(5) 0.109(8) -0.007(5) 0.017(5) -0.005(5) C149 0.046(5) 0.034(5) 0.079(6) -0.001(4) -0.002(4) 0.006(4) C150 0.043(5) 0.056(6) 0.093(7) 0.004(5) -0.003(5) -0.009(5) C151 0.038(5) 0.032(5) 0.085(6) -0.006(4) -0.001(4) 0.005(4) C152 0.052(6) 0.079(7) 0.088(7) 0.000(5) 0.006(5) -0.003(6) C153 0.039(5) 0.085(8) 0.110(9) -0.005(6) 0.008(5) 0.008(5) C155 0.075(7) 0.045(6) 0.118(9) -0.008(5) 0.035(6) -0.018(6) C156 0.050(5) 0.042(5) 0.090(7) -0.004(4) -0.003(5) 0.009(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 S1 O1 1.454(5) . ? S1 O3 1.461(5) . ? S1 O2 1.463(5) . ? S1 N6 1.681(6) . ? F1 C1 1.339(10) . ? F2 C1 1.348(10) . ? F3 C1 1.310(9) . ? F4 C5 1.338(9) . ? F5 C5 1.348(9) . ? F6 C5 1.356(9) . ? N6 C2 1.392(8) . ? C1 C3 1.511(11) . ? C2 C6 1.388(9) . ? C2 C4 1.410(9) . ? C3 C6 1.380(10) . ? C3 C8 1.392(10) . ? C4 C7 1.363(9) . ? C5 C7 1.472(11) . ? C7 C8 1.396(10) . ? S2 O4 1.453(5) . ? S2 O5 1.458(5) . ? S2 O6 1.469(5) . ? S2 N7 1.680(6) . ? F16 C42 1.348(10) . ? F17 C42 1.324(10) . ? F18 C42 1.339(10) . ? F101 C100 1.303(12) . ? F102 C100 1.322(10) . ? F103 C100 1.319(12) . ? N7 C40 1.386(9) . ? C39 C40 1.396(9) . ? C39 C102 1.399(11) . ? C40 C103 1.413(10) . ? C41 C103 1.370(10) . ? C41 C105 1.383(11) . ? C41 C42 1.489(12) . ? C100 C102 1.497(11) . ? C102 C105 1.384(12) . ? N99 C404 1.521(8) . ? N99 C404 1.521(8) 2 ? N99 C403 1.529(8) . ? N99 C403 1.529(8) 2 ? C401 C503 1.519(11) . ? C401 C402 1.539(10) . ? C402 C403 1.510(10) . ? C404 C405 1.527(10) . ? C405 C406 1.547(11) . ? C406 C502 1.531(11) . ? N4 C122 1.510(8) . ? N4 C127 1.524(9) . ? N4 C126 1.527(9) . ? N4 C130 1.534(9) . ? C99 C25 1.510(13) . ? C99 C125 1.532(11) . ? C121 C123 1.506(10) . ? C121 C132 1.546(11) . ? C122 C125 1.483(10) . ? C123 C126 1.506(10) . ? C124 C127 1.505(9) . ? C124 C137 1.542(11) . ? C128 C99B 1.448(17) . ? C128 C99A 1.496(14) . ? C128 C131 1.505(11) . ? C130 C131 1.506(11) . ? C137 C504 1.539(12) . ? N3 C151 1.524(9) . ? N3 C151 1.524(9) 2_655 ? N3 C149 1.528(9) 2_655 ? N3 C149 1.528(9) . ? C148 C155 1.497(12) . ? C148 C149 1.534(11) . ? C150 C156 1.534(11) . ? C150 C153 1.545(12) . ? C151 C156 1.523(11) . ? C152 C155 1.508(12) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O3 112.9(3) . . ? O1 S1 O2 113.8(3) . . ? O3 S1 O2 114.2(3) . . ? O1 S1 N6 107.4(3) . . ? O3 S1 N6 105.4(3) . . ? O2 S1 N6 101.9(3) . . ? C2 N6 S1 124.0(5) . . ? F3 C1 F1 106.4(8) . . ? F3 C1 F2 106.2(8) . . ? F1 C1 F2 105.4(8) . . ? F3 C1 C3 114.4(8) . . ? F1 C1 C3 111.8(7) . . ? F2 C1 C3 112.0(7) . . ? C6 C2 N6 119.3(6) . . ? C6 C2 C4 118.6(6) . . ? N6 C2 C4 122.2(6) . . ? C6 C3 C8 121.3(7) . . ? C6 C3 C1 119.8(8) . . ? C8 C3 C1 118.9(7) . . ? C7 C4 C2 119.5(7) . . ? F4 C5 F5 106.1(7) . . ? F4 C5 F6 104.5(7) . . ? F5 C5 F6 104.7(7) . . ? F4 C5 C7 113.9(7) . . ? F5 C5 C7 113.4(7) . . ? F6 C5 C7 113.3(7) . . ? C3 C6 C2 120.7(7) . . ? C4 C7 C8 122.7(7) . . ? C4 C7 C5 120.3(7) . . ? C8 C7 C5 117.0(7) . . ? C3 C8 C7 117.0(7) . . ? O4 S2 O5 112.7(3) . . ? O4 S2 O6 113.5(3) . . ? O5 S2 O6 115.2(3) . . ? O4 S2 N7 107.0(3) . . ? O5 S2 N7 105.5(3) . . ? O6 S2 N7 101.7(3) . . ? C40 N7 S2 124.4(5) . . ? C40 C39 C102 119.4(8) . . ? N7 C40 C39 122.5(7) . . ? N7 C40 C103 118.3(6) . . ? C39 C40 C103 119.2(7) . . ? C103 C41 C105 121.7(8) . . ? C103 C41 C42 119.1(7) . . ? C105 C41 C42 119.1(8) . . ? F17 C42 F18 106.3(8) . . ? F17 C42 F16 105.4(7) . . ? F18 C42 F16 104.1(8) . . ? F17 C42 C41 113.2(8) . . ? F18 C42 C41 114.7(7) . . ? F16 C42 C41 112.3(8) . . ? F101 C100 F103 104.5(9) . . ? F101 C100 F102 104.5(10) . . ? F103 C100 F102 106.6(9) . . ? F101 C100 C102 115.0(9) . . ? F103 C100 C102 112.8(10) . . ? F102 C100 C102 112.6(8) . . ? C105 C102 C39 121.0(8) . . ? C105 C102 C100 120.0(9) . . ? C39 C102 C100 119.0(9) . . ? C41 C103 C40 119.7(7) . . ? C41 C105 C102 118.9(8) . . ? C404 N99 C404 105.7(7) . 2 ? C404 N99 C403 111.2(4) . . ? C404 N99 C403 110.9(4) 2 . ? C404 N99 C403 110.9(4) . 2 ? C404 N99 C403 111.2(4) 2 2 ? C403 N99 C403 107.1(7) . 2 ? C503 C401 C402 112.6(7) . . ? C403 C402 C401 108.2(6) . . ? C402 C403 N99 114.9(6) . . ? N99 C404 C405 115.6(6) . . ? C404 C405 C406 107.4(7) . . ? C502 C406 C405 111.3(8) . . ? C122 N4 C127 111.3(6) . . ? C122 N4 C126 111.2(6) . . ? C127 N4 C126 106.0(5) . . ? C122 N4 C130 106.0(6) . . ? C127 N4 C130 111.1(6) . . ? C126 N4 C130 111.3(5) . . ? C25 C99 C125 114.0(9) . . ? C123 C121 C132 113.5(7) . . ? C125 C122 N4 117.0(6) . . ? C126 C123 C121 109.9(7) . . ? C127 C124 C137 109.7(6) . . ? C122 C125 C99 110.8(8) . . ? C123 C126 N4 117.3(6) . . ? C124 C127 N4 115.8(6) . . ? C99B C128 C99A 88.8(14) . . ? C99B C128 C131 129.3(16) . . ? C99A C128 C131 111.4(10) . . ? C131 C130 N4 116.4(6) . . ? C128 C131 C130 111.0(8) . . ? C504 C137 C124 111.4(8) . . ? C151 N3 C151 107.8(8) . 2_655 ? C151 N3 C149 110.7(5) . 2_655 ? C151 N3 C149 109.6(4) 2_655 2_655 ? C151 N3 C149 109.6(4) . . ? C151 N3 C149 110.7(5) 2_655 . ? C149 N3 C149 108.5(9) 2_655 . ? C155 C148 C149 112.4(7) . . ? N3 C149 C148 115.2(6) . . ? C156 C150 C153 110.9(7) . . ? C156 C151 N3 114.6(6) . . ? C148 C155 C152 114.3(8) . . ? C151 C156 C150 110.7(7) . . ? _diffrn_measured_fraction_theta_max 0.871 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.871 _refine_diff_density_max 0.317 _refine_diff_density_min -0.486 _refine_diff_density_rms 0.068 _iucr_refine_instructions_details ; TITL SHELX in C2/c CELL 0.71073 23.9400 16.8390 29.8300 90.000 109.479 90.000 ZERR 16.00 0.0190 0.0110 0.0200 0.000 0.011 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H F N O S UNIT 384 640 96 32 48 16 MERG 2 OMIT -8 2 10 OMIT 1 1 5 OMIT -10 4 7 SHEL 7 0.84 DFIX 1.566 C128 C99A DFIX 1.566 C128 C99B SIMU C99A C99B FMAP 2 PLAN 20 SIZE 0.08 0.08 0.22 ACTA 55.00 L.S. 5 WGHT 0.015900 120.044800 FVAR 0.82978 0.66416 S1 6 -0.035471 0.415703 0.315794 11.00000 0.03031 0.03713 = 0.04252 -0.00286 0.00713 0.00162 F1 3 0.259554 0.344795 0.370539 11.00000 0.04797 0.09034 = 0.10262 -0.00875 0.03716 0.00503 F2 3 0.258812 0.465263 0.392834 11.00000 0.04333 0.06684 = 0.15648 0.01651 0.03705 -0.00839 F3 3 0.289530 0.373287 0.443999 11.00000 0.03472 0.13039 = 0.08701 0.01201 0.00173 0.00872 F4 3 0.115282 0.394970 0.519140 11.00000 0.15562 0.08233 = 0.05363 -0.02458 0.04620 -0.02574 F5 3 0.145416 0.276108 0.514879 11.00000 0.06813 0.10333 = 0.06612 0.03281 0.01157 0.01752 F6 3 0.053501 0.305454 0.483680 11.00000 0.06838 0.08333 = 0.05178 0.00925 0.02651 0.00730 O1 5 -0.033015 0.483982 0.346245 11.00000 0.03632 0.04009 = 0.05239 -0.00771 0.01105 -0.00087 O2 5 -0.063612 0.432298 0.265087 11.00000 0.03001 0.05822 = 0.04153 0.00264 0.00307 0.00869 O3 5 -0.057199 0.343991 0.332147 11.00000 0.03566 0.02721 = 0.05294 -0.00153 0.01138 -0.00801 N6 4 0.034406 0.394660 0.319023 11.00000 0.02222 0.04712 = 0.04082 -0.00001 0.00778 0.00305 AFIX 43 H6 2 0.041950 0.390903 0.292862 11.00000 -1.20000 AFIX 0 C1 1 0.248430 0.390095 0.403464 11.00000 0.03463 0.07794 = 0.06869 0.00374 0.00862 0.00404 C2 1 0.080793 0.382947 0.361459 11.00000 0.02526 0.03204 = 0.04591 0.00252 0.00492 0.00461 C3 1 0.185786 0.379182 0.403450 11.00000 0.02436 0.04689 = 0.06487 0.00322 0.00275 0.00437 C4 1 0.071000 0.362578 0.404079 11.00000 0.02745 0.03525 = 0.05400 -0.00846 0.00963 -0.00265 AFIX 43 H4 2 0.032609 0.355980 0.404499 11.00000 -1.20000 AFIX 0 C5 1 0.108736 0.333110 0.489699 11.00000 0.05117 0.05208 = 0.05507 -0.00099 -0.00047 -0.00237 C6 1 0.138736 0.390987 0.362051 11.00000 0.03163 0.03792 = 0.05062 0.00450 0.01555 0.00553 AFIX 43 H6A 2 0.145943 0.404478 0.334243 11.00000 -1.20000 AFIX 0 C7 1 0.118172 0.352628 0.444647 11.00000 0.04139 0.04106 = 0.03731 -0.00020 0.00676 0.00118 C8 1 0.176785 0.359082 0.445807 11.00000 0.03355 0.04880 = 0.04571 -0.00171 -0.00387 0.00229 AFIX 43 H8 2 0.208413 0.350344 0.473636 11.00000 -1.20000 AFIX 0 S2 6 0.397240 0.411483 0.204966 11.00000 0.03104 0.03742 = 0.04737 -0.00048 0.00027 0.00256 F16 3 0.553873 0.462510 0.042543 11.00000 0.10522 0.09262 = 0.09168 0.02483 0.03953 0.02396 F17 3 0.563559 0.337020 0.042561 11.00000 0.09873 0.09417 = 0.09874 -0.03591 0.05237 0.00435 F18 3 0.603891 0.403429 0.105920 11.00000 0.05758 0.12211 = 0.05772 0.00875 0.02113 0.01218 F101 3 0.292099 0.339031 0.031156 11.00000 0.05430 0.21815 = 0.07058 -0.04819 -0.01598 0.00934 F102 3 0.337617 0.294330 -0.011618 11.00000 0.08619 0.11756 = 0.07776 -0.05180 -0.00878 0.01095 F103 3 0.319231 0.417252 -0.011183 11.00000 0.13640 0.08219 = 0.13467 0.01425 -0.08526 0.01409 O4 5 0.369567 0.483358 0.180613 11.00000 0.03901 0.03299 = 0.05022 0.00110 0.00406 0.00599 O5 5 0.358110 0.342714 0.192245 11.00000 0.04308 0.03491 = 0.05998 -0.00149 0.00184 -0.00054 O6 5 0.427643 0.422664 0.256171 11.00000 0.03046 0.04986 = 0.04125 -0.00159 -0.00127 0.00167 N7 4 0.454171 0.390474 0.185908 11.00000 0.03014 0.04983 = 0.04195 0.00524 0.00207 0.01357 AFIX 43 H7 2 0.488367 0.382729 0.207002 11.00000 -1.20000 AFIX 0 C39 1 0.395929 0.371505 0.102296 11.00000 0.03930 0.03447 = 0.05541 -0.00925 0.00237 0.00653 AFIX 43 H39 2 0.361202 0.365770 0.109470 11.00000 -1.20000 AFIX 0 C40 1 0.449764 0.384776 0.138485 11.00000 0.03599 0.03467 = 0.04226 0.00462 -0.00139 0.01126 C41 1 0.499059 0.387619 0.080168 11.00000 0.04682 0.03902 = 0.06091 -0.00648 0.00668 0.02056 C42 1 0.554379 0.396543 0.068260 11.00000 0.07265 0.06679 = 0.04727 0.00676 0.01219 0.01354 C100 1 0.336483 0.354519 0.016502 11.00000 0.05273 0.09741 = 0.05622 -0.01533 -0.00789 0.02997 C102 1 0.394666 0.366906 0.055144 11.00000 0.06039 0.05419 = 0.04434 -0.01498 -0.01821 0.01771 C103 1 0.501936 0.393017 0.126708 11.00000 0.04613 0.04134 = 0.04204 -0.00331 0.00291 0.00955 AFIX 43 H103 2 0.538083 0.402068 0.150448 11.00000 -1.20000 AFIX 0 C105 1 0.445906 0.375762 0.043843 11.00000 0.07625 0.06112 = 0.04164 -0.00574 0.00038 0.02341 AFIX 43 H105 2 0.444617 0.373774 0.012356 11.00000 -1.20000 AFIX 0 N99 4 0.000000 0.164668 0.250000 10.50000 0.04974 0.02523 = 0.05065 0.00000 0.02209 0.00000 C401 1 -0.032991 0.091430 0.120446 11.00000 0.08699 0.06321 = 0.05100 -0.00993 0.03342 0.00605 AFIX 23 H40A 2 0.004049 0.062612 0.127642 11.00000 -1.20000 H40B 2 -0.063598 0.053615 0.120344 11.00000 -1.20000 AFIX 0 C402 1 -0.027112 0.153588 0.159578 11.00000 0.05542 0.04685 = 0.05008 -0.00134 0.02095 -0.00178 AFIX 23 H40C 2 0.003764 0.191450 0.160435 11.00000 -1.20000 H40D 2 -0.064098 0.182257 0.153203 11.00000 -1.20000 AFIX 0 C403 1 -0.011804 0.110683 0.206592 11.00000 0.06002 0.03550 = 0.05159 -0.00685 0.02778 0.00242 AFIX 23 H40E 2 0.023101 0.078372 0.210710 11.00000 -1.20000 H40F 2 -0.044131 0.075100 0.205404 11.00000 -1.20000 AFIX 0 C404 1 0.052459 0.219238 0.255387 11.00000 0.03774 0.04271 = 0.05055 -0.00093 0.01154 -0.00813 AFIX 23 H40G 2 0.058561 0.251895 0.283406 11.00000 -1.20000 H40H 2 0.042391 0.254464 0.228117 11.00000 -1.20000 AFIX 0 C405 1 0.110766 0.177751 0.259733 11.00000 0.04863 0.05720 = 0.06908 0.00824 0.02413 0.00222 AFIX 23 H40I 2 0.107117 0.148841 0.230767 11.00000 -1.20000 H40J 2 0.121153 0.140439 0.286008 11.00000 -1.20000 AFIX 0 C406 1 0.158932 0.242675 0.268482 11.00000 0.03908 0.07537 = 0.07520 0.02523 0.01012 0.00103 AFIX 23 H40K 2 0.146750 0.281517 0.243048 11.00000 -1.20000 H40L 2 0.163185 0.269760 0.298138 11.00000 -1.20000 AFIX 0 C502 1 0.218638 0.206986 0.270742 11.00000 0.04866 0.11839 = 0.09232 0.03498 0.02500 0.00943 AFIX 137 H50A 2 0.231252 0.169556 0.296437 11.00000 -1.50000 H50B 2 0.247538 0.248562 0.275876 11.00000 -1.50000 H50C 2 0.214557 0.180466 0.241329 11.00000 -1.50000 AFIX 0 C503 1 -0.048280 0.128354 0.071360 11.00000 0.13032 0.06990 = 0.05760 0.00551 0.04474 0.00418 AFIX 137 H50D 2 -0.084380 0.158130 0.064368 11.00000 -1.50000 H50E 2 -0.053312 0.087177 0.048084 11.00000 -1.50000 H50F 2 -0.016810 0.163094 0.070605 11.00000 -1.50000 AFIX 0 N4 4 0.187989 0.405809 0.118157 11.00000 0.03098 0.04219 = 0.05398 -0.00895 0.00996 -0.00166 C99 1 0.054902 0.416286 0.000347 11.00000 0.03404 0.13456 = 0.09670 0.01974 0.00366 -0.00923 AFIX 23 H99A 2 0.028470 0.388035 0.013352 11.00000 -1.20000 H99B 2 0.046721 0.472569 0.001264 11.00000 -1.20000 AFIX 0 C25 1 0.041462 0.391515 -0.050840 11.00000 0.06228 0.17947 = 0.07026 0.01317 -0.00619 0.02643 AFIX 137 H25A 2 0.070262 0.414369 -0.062993 11.00000 -1.50000 H25B 2 0.002634 0.409754 -0.069393 11.00000 -1.50000 H25C 2 0.042948 0.334676 -0.052669 11.00000 -1.50000 AFIX 0 C121 1 0.278718 0.571242 0.084123 11.00000 0.04535 0.03869 = 0.07254 0.01710 0.00686 0.00856 AFIX 23 H12A 2 0.263177 0.558940 0.050453 11.00000 -1.20000 H12B 2 0.316773 0.544976 0.097223 11.00000 -1.20000 AFIX 0 C122 1 0.128022 0.423314 0.081951 11.00000 0.02631 0.04455 = 0.06805 -0.00573 0.00501 -0.00070 AFIX 23 H12C 2 0.098286 0.396376 0.091881 11.00000 -1.20000 H12D 2 0.120774 0.479891 0.082715 11.00000 -1.20000 AFIX 0 C123 1 0.237100 0.538491 0.107870 11.00000 0.03094 0.05617 = 0.07323 0.00228 0.01421 -0.00582 AFIX 23 H12E 2 0.249448 0.556019 0.140708 11.00000 -1.20000 H12F 2 0.197354 0.558216 0.091845 11.00000 -1.20000 AFIX 0 C124 1 0.156493 0.261794 0.124608 11.00000 0.05007 0.05268 = 0.08584 -0.00868 0.04488 -0.01272 AFIX 23 H12G 2 0.120656 0.266177 0.097238 11.00000 -1.20000 H12H 2 0.146946 0.275843 0.152750 11.00000 -1.20000 AFIX 0 C125 1 0.118955 0.400575 0.031984 11.00000 0.03388 0.06133 = 0.07504 0.00298 -0.00156 0.00316 AFIX 23 H12I 2 0.128013 0.344670 0.030601 11.00000 -1.20000 H12J 2 0.145727 0.430798 0.020280 11.00000 -1.20000 AFIX 0 C126 1 0.237148 0.449139 0.106051 11.00000 0.03310 0.04385 = 0.04584 -0.00470 0.00869 -0.00886 AFIX 23 H12K 2 0.274863 0.430648 0.127726 11.00000 -1.20000 H12L 2 0.235092 0.433365 0.074265 11.00000 -1.20000 AFIX 0 C127 1 0.202820 0.317658 0.119073 11.00000 0.03539 0.03729 = 0.05667 -0.00683 0.01849 -0.00020 AFIX 23 H12M 2 0.209945 0.304594 0.089772 11.00000 -1.20000 H12N 2 0.239454 0.308363 0.145050 11.00000 -1.20000 AFIX 0 C128 1 0.231461 0.455174 0.252978 11.00000 0.08616 0.15988 = 0.07402 -0.05418 0.03194 -0.01584 PART 1 AFIX 23 H12O 2 0.209132 0.504371 0.246148 21.00000 -1.20000 H12P 2 0.208569 0.416604 0.263684 21.00000 -1.20000 PART 2 H12Q 2 0.204070 0.417871 0.259229 -21.00000 -1.20000 H12R 2 0.269162 0.446734 0.277935 -21.00000 -1.20000 AFIX 0 PART 1 C99A 1 0.289303 0.469150 0.291611 21.00000 0.20259 0.13254 = 0.05564 -0.01526 0.04895 -0.05297 AFIX 137 H99C 2 0.317695 0.488980 0.278020 21.00000 -1.50000 H99D 2 0.303405 0.420127 0.307876 21.00000 -1.50000 H99E 2 0.283939 0.507316 0.313735 21.00000 -1.50000 AFIX 0 PART 2 C99B 1 0.211953 0.532568 0.262890 -21.00000 0.06031 0.05637 = 0.07348 -0.00490 0.00756 -0.01517 AFIX 137 H99F 2 0.205888 0.531392 0.293113 -21.00000 -1.50000 H99G 2 0.175468 0.546152 0.238467 -21.00000 -1.50000 H99H 2 0.241568 0.571479 0.263661 -21.00000 -1.50000 AFIX 0 PART 0 C130 1 0.184560 0.433083 0.166225 11.00000 0.05460 0.04879 = 0.06780 -0.00927 0.03046 0.00293 AFIX 23 H13A 2 0.172519 0.488376 0.163369 11.00000 -1.20000 H13B 2 0.153670 0.402796 0.172753 11.00000 -1.20000 AFIX 0 C131 1 0.240497 0.425314 0.208344 11.00000 0.05550 0.05823 = 0.05957 -0.00545 0.02295 -0.00839 AFIX 23 H13C 2 0.252504 0.370027 0.212461 11.00000 -1.20000 H13D 2 0.271938 0.455428 0.202528 11.00000 -1.20000 AFIX 0 C132 1 0.288086 0.661949 0.090213 11.00000 0.05369 0.05540 = 0.08265 0.01369 0.00032 -0.01235 AFIX 137 H13E 2 0.250478 0.688385 0.078314 11.00000 -1.50000 H13F 2 0.313054 0.679533 0.072806 11.00000 -1.50000 H13G 2 0.306543 0.674266 0.123301 11.00000 -1.50000 AFIX 0 C137 1 0.179829 0.175795 0.129072 11.00000 0.10617 0.05001 = 0.08266 -0.01446 0.06428 -0.01004 AFIX 23 H13W 2 0.195024 0.164830 0.103358 11.00000 -1.20000 H13X 2 0.212222 0.169907 0.158852 11.00000 -1.20000 AFIX 0 C504 1 0.130787 0.115553 0.127350 11.00000 0.17790 0.05055 = 0.16570 -0.02710 0.12338 -0.02770 AFIX 137 H50G 2 0.116279 0.125584 0.153185 11.00000 -1.50000 H50H 2 0.146597 0.062694 0.130068 11.00000 -1.50000 H50I 2 0.098904 0.120812 0.097724 11.00000 -1.50000 AFIX 0 N3 4 0.500000 0.162551 0.250000 10.50000 0.04183 0.03437 = 0.08159 0.00000 -0.00032 0.00000 C148 1 0.426876 0.171471 0.296964 11.00000 0.05258 0.03352 = 0.10913 -0.00728 0.01658 -0.00521 AFIX 23 H14A 2 0.392970 0.148559 0.272658 11.00000 -1.20000 H14B 2 0.449654 0.128332 0.315997 11.00000 -1.20000 AFIX 0 C149 1 0.465385 0.215598 0.273006 11.00000 0.04604 0.03413 = 0.07923 -0.00056 -0.00216 0.00627 AFIX 23 H14C 2 0.440079 0.250433 0.248794 11.00000 -1.20000 H14D 2 0.493320 0.248763 0.296611 11.00000 -1.20000 AFIX 0 C150 1 0.367600 0.096269 0.139396 11.00000 0.04297 0.05636 = 0.09254 0.00420 -0.00338 -0.00940 AFIX 23 H15A 2 0.345067 0.073030 0.157751 11.00000 -1.20000 H15B 2 0.387271 0.053598 0.128672 11.00000 -1.20000 AFIX 0 C151 1 0.457182 0.109260 0.212955 11.00000 0.03841 0.03225 = 0.08483 -0.00601 -0.00103 0.00495 AFIX 23 H15C 2 0.479968 0.072334 0.201006 11.00000 -1.20000 H15D 2 0.434540 0.078391 0.228349 11.00000 -1.20000 AFIX 0 C152 1 0.371190 0.182779 0.355163 11.00000 0.05235 0.07852 = 0.08812 0.00020 0.00578 -0.00316 AFIX 137 H15X 2 0.335636 0.160610 0.333181 11.00000 -1.50000 H15Y 2 0.361059 0.220005 0.375589 11.00000 -1.50000 H15Z 2 0.395014 0.141024 0.373998 11.00000 -1.50000 AFIX 0 C153 1 0.325093 0.140178 0.095850 11.00000 0.03907 0.08486 = 0.11010 -0.00478 0.00784 0.00833 AFIX 137 H15R 2 0.304493 0.181094 0.106440 11.00000 -1.50000 H15I 2 0.296954 0.103172 0.076235 11.00000 -1.50000 H15J 2 0.347427 0.163545 0.077823 11.00000 -1.50000 AFIX 0 C155 1 0.405526 0.224711 0.328028 11.00000 0.07500 0.04528 = 0.11796 -0.00751 0.03547 -0.01802 AFIX 23 H15E 2 0.380566 0.265606 0.308394 11.00000 -1.20000 H15F 2 0.439472 0.250772 0.350577 11.00000 -1.20000 AFIX 0 C156 1 0.414179 0.153354 0.170980 11.00000 0.05024 0.04204 = 0.09040 -0.00435 -0.00346 0.00873 AFIX 23 H15G 2 0.435877 0.177911 0.152379 11.00000 -1.20000 H15H 2 0.394603 0.195053 0.182590 11.00000 -1.20000 HKLF 4 1.0 -1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 -1.00 END ; data_shelx2 _database_code_depnum_ccdc_archive 'CCDC 910543' #TrackingRef '0207.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C42 H53 F18 N4 O4 P' _chemical_formula_weight 1050.85 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 0.0000 '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' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.376(5) _cell_length_b 24.910(13) _cell_length_c 10.433(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.512(9) _cell_angle_gamma 90.00 _cell_volume 2434(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5182 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1084 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9669 _exptl_absorpt_correction_T_max 0.9983 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12206 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.02 _reflns_number_total 4092 _reflns_number_gt 3549 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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. One of the CF3 groups is modelled as rotationally disordered over 2 positions, geometrical and thermal parameter restraints were applied. ; _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^)+(0.1345P)^2^+1.1420P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4092 _refine_ls_number_parameters 631 _refine_ls_number_restraints 37 _refine_ls_R_factor_all 0.0838 _refine_ls_R_factor_gt 0.0750 _refine_ls_wR_factor_ref 0.2123 _refine_ls_wR_factor_gt 0.1999 _refine_ls_goodness_of_fit_ref 1.081 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1W O 0.0156(7) 0.2471(2) 0.0426(5) 0.0445(14) Uani 1 1 d D . . H1W H 0.074(5) 0.222(2) 0.052(5) 0.067 Uiso 1 1 d D . . H2W H -0.056(7) 0.239(3) -0.005(9) 0.067 Uiso 1 1 d D . . P1 P 0.3597(2) 0.21828(7) 0.94343(16) 0.0325(4) Uani 1 1 d . . . O1 O 0.2801(7) 0.1905(2) 1.0421(5) 0.0456(14) Uani 1 1 d . . . N1 N 0.2485(7) 0.2639(2) 0.8771(6) 0.0357(14) Uani 1 1 d . . . H1 H 0.1600 0.2597 0.8932 0.043 Uiso 1 1 calc R . . N2 N 0.4249(8) 0.1777(2) 0.8367(6) 0.0392(15) Uani 1 1 d . . . H2 H 0.5094 0.1851 0.8130 0.047 Uiso 1 1 calc R . . N3 N 0.5075(7) 0.2504(2) 0.9875(5) 0.0311(13) Uani 1 1 d . . . H3 H 0.5873 0.2338 0.9809 0.037 Uiso 1 1 calc R . . C1 C 0.2782(8) 0.3075(3) 0.7995(6) 0.0302(15) Uani 1 1 d . . . C2 C 0.4070(9) 0.3103(3) 0.7351(6) 0.0321(16) Uani 1 1 d . . . H2A H 0.4707 0.2817 0.7392 0.039 Uiso 1 1 calc R . . C3 C 0.4382(9) 0.3556(3) 0.6661(7) 0.0324(16) Uani 1 1 d . . . C4 C 0.5773(11) 0.3587(3) 0.6024(9) 0.050(2) Uani 1 1 d . . . C5 C 0.3439(10) 0.3981(3) 0.6545(7) 0.0396(19) Uani 1 1 d . . . H5 H 0.3660 0.4286 0.6080 0.048 Uiso 1 1 calc R . . C6 C 0.2172(10) 0.3938(3) 0.7135(8) 0.0409(19) Uani 1 1 d . . . C7 C 0.1136(11) 0.4401(3) 0.7060(9) 0.050(2) Uani 1 1 d . . . C8 C 0.1840(9) 0.3497(3) 0.7880(6) 0.0346(17) Uani 1 1 d . . . H8 H 0.0986 0.3488 0.8299 0.041 Uiso 1 1 calc R . . C9 C 0.3593(11) 0.1322(3) 0.7793(8) 0.045(2) Uani 1 1 d . . . C10 C 0.2223(11) 0.1167(3) 0.7944(9) 0.050(2) Uani 1 1 d . . . H10 H 0.1647 0.1361 0.8481 0.060 Uiso 1 1 calc R . . C11 C 0.1658(11) 0.0701(4) 0.7270(9) 0.052(2) Uani 1 1 d . . . C12 C 0.0187(13) 0.0562(4) 0.7459(13) 0.070(3) Uani 1 1 d . . . C13 C 0.2556(12) 0.0415(4) 0.6545(8) 0.053(2) Uani 1 1 d . . . H13 H 0.2212 0.0108 0.6129 0.063 Uiso 1 1 calc R . . C14 C 0.3934(12) 0.0560(4) 0.6404(9) 0.055(2) Uani 1 1 d . . . C15 C 0.4831(15) 0.0227(4) 0.5597(9) 0.062(3) Uani 1 1 d . . . C16 C 0.4428(13) 0.1008(3) 0.6993(8) 0.055(3) Uani 1 1 d . . . H16 H 0.5362 0.1114 0.6864 0.067 Uiso 1 1 calc R . . C17 C 0.5117(9) 0.3031(3) 1.0350(6) 0.0342(16) Uani 1 1 d . . . C18 C 0.6276(9) 0.3357(3) 1.0121(7) 0.0351(16) Uani 1 1 d . A . H18 H 0.7044 0.3221 0.9689 0.042 Uiso 1 1 calc R . . C19 C 0.6294(10) 0.3879(3) 1.0531(8) 0.045(2) Uani 1 1 d . . . C21 C 0.5178(10) 0.4101(3) 1.1164(8) 0.045(2) Uani 1 1 d . A . H21 H 0.5192 0.4461 1.1404 0.054 Uiso 1 1 calc R . . C22 C 0.4023(9) 0.3771(3) 1.1436(7) 0.0382(17) Uani 1 1 d . . . C23 C 0.2797(10) 0.3979(4) 1.2144(8) 0.047(2) Uani 1 1 d . A . C24 C 0.4002(8) 0.3241(3) 1.1042(6) 0.0332(16) Uani 1 1 d . A . H24 H 0.3239 0.3022 1.1240 0.040 Uiso 1 1 calc R . . F1 F 0.6804(7) 0.3285(3) 0.6592(7) 0.078(2) Uani 1 1 d . . . F2 F 0.5670(8) 0.3455(4) 0.4818(6) 0.103(3) Uani 1 1 d . . . F3 F 0.6358(8) 0.4080(2) 0.6059(9) 0.086(2) Uani 1 1 d . . . F4 F 0.1223(12) 0.4683(4) 0.5996(10) 0.136(4) Uani 1 1 d . . . F5 F 0.1285(8) 0.4732(3) 0.8018(9) 0.099(3) Uani 1 1 d . . . F6 F -0.0216(7) 0.4251(2) 0.7043(6) 0.0674(17) Uani 1 1 d . . . F7 F -0.0736(10) 0.0895(4) 0.6849(14) 0.149(5) Uani 1 1 d . . . F8 F -0.0146(11) 0.0082(4) 0.6970(11) 0.128(4) Uani 1 1 d . . . F9 F -0.0197(11) 0.0562(6) 0.8642(9) 0.149(5) Uani 1 1 d . . . F10 F 0.4390(10) 0.0191(3) 0.4371(6) 0.086(2) Uani 1 1 d . . . F11 F 0.4910(9) -0.0281(2) 0.6006(6) 0.078(2) Uani 1 1 d . . . F12 F 0.6203(9) 0.0397(3) 0.5547(8) 0.096(3) Uani 1 1 d . . . C20B C 0.7553(10) 0.4226(3) 1.0260(9) 0.061(3) Uani 0.465(7) 1 d PD A 1 F13B F 0.8611(17) 0.3964(7) 0.9688(15) 0.0763(18) Uani 0.465(7) 1 d PD A 1 F14B F 0.7365(15) 0.4678(5) 0.9707(15) 0.0763(18) Uani 0.465(7) 1 d PD A 1 F15B F 0.8246(15) 0.4373(6) 1.1431(12) 0.0763(18) Uani 0.465(7) 1 d PD A 1 C20A C 0.7553(10) 0.4226(3) 1.0260(9) 0.061(3) Uani 0.535(7) 1 d PD A 2 F13A F 0.7550(14) 0.4710(4) 1.0762(13) 0.0763(18) Uani 0.535(7) 1 d PD A 2 F14A F 0.7304(13) 0.4426(5) 0.8991(11) 0.0763(18) Uani 0.535(7) 1 d PD A 2 F15A F 0.8754(14) 0.3974(6) 1.0165(14) 0.0763(18) Uani 0.535(7) 1 d PD A 2 F16 F 0.2860(7) 0.3825(2) 1.3380(5) 0.0623(15) Uani 1 1 d . . . F17 F 0.2726(8) 0.4506(2) 1.2154(7) 0.079(2) Uani 1 1 d . . . F18 F 0.1557(8) 0.3780(4) 1.1673(7) 0.093(2) Uani 1 1 d . . . O2 O 0.7722(6) 0.2201(2) 0.9035(4) 0.0397(12) Uani 1 1 d . . . O3 O 0.6636(6) 0.2034(2) 0.7134(5) 0.0401(13) Uani 1 1 d . . . C25 C 0.7718(9) 0.2146(3) 0.7823(6) 0.0353(16) Uani 1 1 d . . . C26 C 0.9103(10) 0.2237(4) 0.7186(7) 0.0467(19) Uani 1 1 d . . . H26A H 0.9112 0.2031 0.6409 0.070 Uiso 1 1 calc R . . H26B H 0.9882 0.2126 0.7754 0.070 Uiso 1 1 calc R . . H26C H 0.9201 0.2611 0.6990 0.070 Uiso 1 1 calc R . . N4 N 0.7030(7) 0.1711(2) 0.2980(5) 0.0335(14) Uani 1 1 d . . . C27 C 0.8283(9) 0.1383(3) 0.3537(7) 0.0356(17) Uani 1 1 d . . . H27A H 0.8689 0.1571 0.4281 0.043 Uiso 1 1 calc R . . H27B H 0.7919 0.1042 0.3833 0.043 Uiso 1 1 calc R . . C28 C 0.9445(10) 0.1272(4) 0.2650(8) 0.0439(19) Uani 1 1 d . . . H28A H 0.9826 0.1610 0.2350 0.053 Uiso 1 1 calc R . . H28B H 0.9059 0.1077 0.1909 0.053 Uiso 1 1 calc R . . C29 C 1.0641(10) 0.0948(3) 0.3299(8) 0.046(2) Uani 1 1 d . . . H29A H 1.0244 0.0627 0.3670 0.055 Uiso 1 1 calc R . . H29B H 1.1083 0.1158 0.3992 0.055 Uiso 1 1 calc R . . C30 C 1.1790(11) 0.0785(4) 0.2361(11) 0.061(3) Uani 1 1 d . . . H30A H 1.1349 0.0596 0.1645 0.092 Uiso 1 1 calc R . . H30B H 1.2481 0.0556 0.2793 0.092 Uiso 1 1 calc R . . H30C H 1.2257 0.1101 0.2059 0.092 Uiso 1 1 calc R . . C31 C 0.7526(9) 0.2272(3) 0.2597(7) 0.0356(17) Uani 1 1 d . . . H31A H 0.8184 0.2232 0.1911 0.043 Uiso 1 1 calc R . . H31B H 0.6703 0.2468 0.2249 0.043 Uiso 1 1 calc R . . C32 C 0.8242(9) 0.2609(3) 0.3636(7) 0.0365(16) Uani 1 1 d . . . H32A H 0.9146 0.2447 0.3909 0.044 Uiso 1 1 calc R . . H32B H 0.7644 0.2624 0.4371 0.044 Uiso 1 1 calc R . . C33 C 0.8496(10) 0.3173(3) 0.3147(8) 0.045(2) Uani 1 1 d . . . H33A H 0.9026 0.3153 0.2371 0.055 Uiso 1 1 calc R . . H33B H 0.7583 0.3341 0.2930 0.055 Uiso 1 1 calc R . . C34 C 0.9306(11) 0.3515(4) 0.4115(8) 0.049(2) Uani 1 1 d . . . H34A H 0.8782 0.3538 0.4883 0.074 Uiso 1 1 calc R . . H34B H 0.9431 0.3868 0.3770 0.074 Uiso 1 1 calc R . . H34C H 1.0224 0.3357 0.4311 0.074 Uiso 1 1 calc R . . C35 C 0.5944(9) 0.1740(3) 0.4004(6) 0.0355(17) Uani 1 1 d . . . H35A H 0.6415 0.1873 0.4787 0.043 Uiso 1 1 calc R . . H35B H 0.5612 0.1379 0.4172 0.043 Uiso 1 1 calc R . . C36 C 0.4650(9) 0.2094(3) 0.3683(7) 0.0380(17) Uani 1 1 d . . . H36A H 0.4195 0.1981 0.2875 0.046 Uiso 1 1 calc R . . H36B H 0.4950 0.2464 0.3597 0.046 Uiso 1 1 calc R . . C37 C 0.3588(9) 0.2048(3) 0.4755(7) 0.0397(18) Uani 1 1 d . . . H37A H 0.3257 0.1680 0.4808 0.048 Uiso 1 1 calc R . . H37B H 0.4067 0.2139 0.5569 0.048 Uiso 1 1 calc R . . C38 C 0.2314(10) 0.2419(4) 0.4516(8) 0.049(2) Uani 1 1 d . . . H38A H 0.2641 0.2783 0.4454 0.073 Uiso 1 1 calc R . . H38B H 0.1683 0.2389 0.5213 0.073 Uiso 1 1 calc R . . H38C H 0.1813 0.2319 0.3729 0.073 Uiso 1 1 calc R . . C39 C 0.6395(9) 0.1446(3) 0.1773(6) 0.0345(16) Uani 1 1 d . . . H39A H 0.7088 0.1469 0.1112 0.041 Uiso 1 1 calc R . . H39B H 0.5563 0.1651 0.1479 0.041 Uiso 1 1 calc R . . C40 C 0.5951(9) 0.0859(3) 0.1910(7) 0.0382(17) Uani 1 1 d . . . H40A H 0.5217 0.0832 0.2534 0.046 Uiso 1 1 calc R . . H40B H 0.6766 0.0649 0.2220 0.046 Uiso 1 1 calc R . . C41 C 0.5385(11) 0.0634(3) 0.0629(8) 0.050(2) Uani 1 1 d . . . H41A H 0.4975 0.0283 0.0773 0.060 Uiso 1 1 calc R . . H41B H 0.4627 0.0866 0.0290 0.060 Uiso 1 1 calc R . . C42 C 0.6498(13) 0.0583(4) -0.0355(8) 0.062(3) Uani 1 1 d . . . H42A H 0.6840 0.0933 -0.0572 0.092 Uiso 1 1 calc R . . H42B H 0.6088 0.0413 -0.1111 0.092 Uiso 1 1 calc R . . H42C H 0.7278 0.0370 -0.0013 0.092 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 O1W 0.036(4) 0.063(4) 0.035(3) -0.006(3) 0.006(2) -0.008(3) P1 0.0321(11) 0.0334(9) 0.0319(9) 0.0058(8) 0.0020(7) -0.0021(8) O1 0.037(4) 0.054(3) 0.046(3) 0.026(3) 0.003(2) -0.008(3) N1 0.029(4) 0.038(3) 0.040(3) 0.006(3) 0.007(3) -0.003(3) N2 0.044(5) 0.032(3) 0.042(3) -0.004(3) -0.004(3) -0.003(3) N3 0.028(4) 0.034(3) 0.031(3) -0.001(2) 0.003(2) 0.001(2) C1 0.036(5) 0.029(3) 0.027(3) 0.002(3) 0.005(3) -0.004(3) C2 0.036(5) 0.028(3) 0.032(3) 0.004(3) 0.000(3) 0.004(3) C3 0.031(5) 0.032(4) 0.035(4) 0.005(3) 0.007(3) 0.003(3) C4 0.052(7) 0.036(4) 0.063(5) 0.018(4) 0.022(4) 0.015(4) C5 0.046(6) 0.033(4) 0.041(4) 0.012(3) 0.015(4) 0.011(3) C6 0.045(6) 0.030(4) 0.047(4) -0.003(3) 0.000(4) 0.003(3) C7 0.040(6) 0.042(4) 0.068(6) 0.003(4) 0.021(4) 0.014(4) C8 0.042(5) 0.034(4) 0.028(3) 0.004(3) 0.006(3) 0.004(3) C9 0.063(7) 0.026(3) 0.045(4) 0.011(3) -0.018(4) -0.006(3) C10 0.043(6) 0.044(5) 0.061(5) 0.009(4) -0.007(4) 0.003(4) C11 0.045(6) 0.056(5) 0.056(5) 0.015(4) 0.003(4) -0.006(4) C12 0.056(8) 0.060(6) 0.092(8) -0.001(6) -0.006(6) -0.014(5) C13 0.061(7) 0.054(5) 0.043(5) 0.009(4) -0.003(4) 0.005(4) C14 0.070(8) 0.043(5) 0.051(5) 0.007(4) -0.001(5) -0.005(4) C15 0.092(9) 0.047(5) 0.046(5) 0.000(4) 0.002(5) 0.010(5) C16 0.098(9) 0.032(4) 0.036(4) 0.002(3) -0.003(4) -0.002(4) C17 0.028(4) 0.047(4) 0.027(3) 0.001(3) -0.004(3) 0.003(3) C18 0.029(5) 0.046(4) 0.031(3) -0.005(3) 0.005(3) -0.005(3) C19 0.035(5) 0.048(5) 0.052(5) -0.001(4) 0.011(4) -0.005(4) C21 0.046(6) 0.037(4) 0.053(5) -0.012(4) 0.015(4) -0.003(3) C22 0.038(5) 0.044(4) 0.033(3) 0.003(3) 0.004(3) -0.001(3) C23 0.035(6) 0.063(5) 0.042(4) -0.009(4) 0.005(4) 0.005(4) C24 0.029(4) 0.040(4) 0.030(3) 0.002(3) -0.001(3) -0.002(3) F1 0.039(4) 0.091(4) 0.105(5) 0.053(4) 0.033(3) 0.024(3) F2 0.060(6) 0.195(9) 0.057(3) -0.017(5) 0.030(3) -0.002(5) F3 0.048(4) 0.060(4) 0.154(7) 0.027(4) 0.036(4) 0.002(3) F4 0.149(9) 0.110(6) 0.158(7) 0.093(6) 0.098(7) 0.095(6) F5 0.077(6) 0.055(3) 0.163(7) -0.057(4) -0.028(5) 0.029(3) F6 0.052(4) 0.052(3) 0.098(4) -0.005(3) -0.005(3) 0.021(3) F7 0.054(6) 0.102(6) 0.289(15) 0.065(8) -0.026(7) -0.001(4) F8 0.096(8) 0.097(6) 0.192(9) -0.041(6) 0.034(7) -0.046(5) F9 0.088(8) 0.251(14) 0.110(6) -0.053(8) 0.032(5) -0.078(8) F10 0.119(7) 0.084(5) 0.054(3) 0.009(3) 0.005(4) 0.020(4) F11 0.117(6) 0.053(3) 0.065(3) 0.016(3) 0.009(4) 0.001(3) F12 0.079(6) 0.075(4) 0.138(6) -0.044(4) 0.041(5) -0.014(4) C20B 0.052(7) 0.044(5) 0.088(7) -0.034(5) 0.031(5) -0.019(4) F13B 0.063(4) 0.074(3) 0.094(5) -0.018(3) 0.022(4) -0.032(2) F14B 0.063(4) 0.074(3) 0.094(5) -0.018(3) 0.022(4) -0.032(2) F15B 0.063(4) 0.074(3) 0.094(5) -0.018(3) 0.022(4) -0.032(2) C20A 0.052(7) 0.044(5) 0.088(7) -0.034(5) 0.031(5) -0.019(4) F13A 0.063(4) 0.074(3) 0.094(5) -0.018(3) 0.022(4) -0.032(2) F14A 0.063(4) 0.074(3) 0.094(5) -0.018(3) 0.022(4) -0.032(2) F15A 0.063(4) 0.074(3) 0.094(5) -0.018(3) 0.022(4) -0.032(2) F16 0.069(4) 0.065(3) 0.055(3) 0.002(3) 0.030(3) 0.007(3) F17 0.084(5) 0.054(3) 0.103(5) 0.013(3) 0.056(4) 0.024(3) F18 0.054(5) 0.138(6) 0.087(4) -0.050(5) 0.012(4) 0.007(4) O2 0.040(3) 0.049(3) 0.030(2) 0.003(2) 0.003(2) 0.003(3) O3 0.038(4) 0.050(3) 0.032(2) -0.005(2) -0.004(2) 0.002(2) C25 0.039(5) 0.034(4) 0.034(3) -0.005(3) 0.000(3) 0.005(3) C26 0.042(5) 0.062(5) 0.037(4) 0.003(4) 0.005(3) 0.007(4) N4 0.037(4) 0.036(3) 0.028(3) 0.006(2) 0.002(3) -0.002(3) C27 0.029(5) 0.043(4) 0.034(4) 0.005(3) -0.001(3) 0.000(3) C28 0.036(5) 0.052(5) 0.044(4) 0.010(4) 0.006(3) -0.002(3) C29 0.044(6) 0.040(4) 0.052(5) 0.008(4) -0.001(4) -0.007(3) C30 0.035(6) 0.064(6) 0.086(7) 0.023(5) 0.015(5) 0.016(4) C31 0.042(5) 0.032(4) 0.033(3) 0.004(3) 0.003(3) 0.006(3) C32 0.027(4) 0.042(4) 0.040(4) -0.002(3) 0.002(3) 0.000(3) C33 0.047(6) 0.051(5) 0.040(4) -0.009(4) 0.016(4) -0.004(4) C34 0.041(6) 0.052(5) 0.056(5) -0.009(4) 0.013(4) -0.012(4) C35 0.037(5) 0.043(4) 0.028(3) 0.001(3) 0.007(3) 0.004(3) C36 0.032(5) 0.050(5) 0.032(3) 0.004(3) 0.004(3) 0.002(3) C37 0.029(5) 0.056(5) 0.034(3) -0.003(3) 0.006(3) -0.001(3) C38 0.034(6) 0.070(6) 0.042(4) 0.005(4) 0.006(4) 0.008(4) C39 0.038(5) 0.039(4) 0.027(3) -0.005(3) 0.000(3) 0.005(3) C40 0.038(5) 0.042(4) 0.035(4) -0.005(3) 0.004(3) -0.006(3) C41 0.063(7) 0.043(5) 0.044(4) 0.002(4) -0.008(4) -0.006(4) C42 0.092(9) 0.045(5) 0.048(5) -0.005(4) 0.008(5) 0.013(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.470(6) . ? P1 N2 1.641(7) . ? P1 N3 1.649(7) . ? P1 N1 1.671(6) . ? N1 C1 1.391(9) . ? N2 C9 1.410(10) . ? N3 C17 1.402(10) . ? C1 C8 1.375(11) . ? C1 C2 1.410(11) . ? C2 C3 1.376(10) . ? C3 C5 1.382(11) . ? C3 C4 1.492(12) . ? C4 F2 1.300(11) . ? C4 F3 1.344(11) . ? C4 F1 1.343(10) . ? C5 C6 1.366(12) . ? C6 C8 1.389(11) . ? C6 C7 1.506(11) . ? C7 F5 1.299(11) . ? C7 F4 1.319(11) . ? C7 F6 1.321(12) . ? C9 C10 1.357(14) . ? C9 C16 1.408(14) . ? C10 C11 1.446(13) . ? C11 C13 1.358(14) . ? C11 C12 1.444(16) . ? C12 F9 1.301(15) . ? C12 F8 1.332(13) . ? C12 F7 1.339(14) . ? C13 C14 1.356(15) . ? C14 C16 1.345(13) . ? C14 C15 1.471(15) . ? C15 F11 1.338(11) . ? C15 F10 1.330(11) . ? C15 F12 1.358(15) . ? C17 C18 1.386(11) . ? C17 C24 1.398(11) . ? C18 C19 1.368(12) . ? C19 C21 1.378(13) . ? C19 C20B 1.500(12) . ? C21 C22 1.398(12) . ? C22 C24 1.383(11) . ? C22 C23 1.487(12) . ? C23 F17 1.314(11) . ? C23 F18 1.338(12) . ? C23 F16 1.344(10) . ? C20B F14B 1.272(12) . ? C20B F13B 1.349(13) . ? C20B F15B 1.407(12) . ? O2 C25 1.272(8) . ? O3 C25 1.248(9) . ? C25 C26 1.501(12) . ? N4 C35 1.509(10) . ? N4 C39 1.519(9) . ? N4 C27 1.526(10) . ? N4 C31 1.530(9) . ? C27 C28 1.486(12) . ? C28 C29 1.518(12) . ? C29 C30 1.542(13) . ? C31 C32 1.506(11) . ? C32 C33 1.516(11) . ? C33 C34 1.502(12) . ? C35 C36 1.525(11) . ? C36 C37 1.533(10) . ? C37 C38 1.523(12) . ? C39 C40 1.529(11) . ? C40 C41 1.523(11) . ? C41 C42 1.501(14) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 N2 113.6(4) . . ? O1 P1 N3 118.7(3) . . ? N2 P1 N3 98.9(3) . . ? O1 P1 N1 106.5(4) . . ? N2 P1 N1 112.4(3) . . ? N3 P1 N1 106.7(3) . . ? C1 N1 P1 129.4(6) . . ? C9 N2 P1 127.9(7) . . ? C17 N3 P1 124.3(5) . . ? C8 C1 N1 120.3(7) . . ? C8 C1 C2 118.7(6) . . ? N1 C1 C2 120.9(7) . . ? C3 C2 C1 119.7(7) . . ? C2 C3 C5 121.6(8) . . ? C2 C3 C4 119.1(7) . . ? C5 C3 C4 119.3(7) . . ? F2 C4 F3 105.8(8) . . ? F2 C4 F1 107.8(8) . . ? F3 C4 F1 102.5(9) . . ? F2 C4 C3 112.9(9) . . ? F3 C4 C3 113.5(7) . . ? F1 C4 C3 113.5(7) . . ? C3 C5 C6 117.8(7) . . ? C5 C6 C8 122.3(8) . . ? C5 C6 C7 119.2(7) . . ? C8 C6 C7 118.3(8) . . ? F5 C7 F4 107.5(9) . . ? F5 C7 F6 105.1(8) . . ? F4 C7 F6 103.5(9) . . ? F5 C7 C6 113.5(8) . . ? F4 C7 C6 112.8(7) . . ? F6 C7 C6 113.6(7) . . ? C1 C8 C6 119.7(8) . . ? C10 C9 N2 125.3(9) . . ? C10 C9 C16 117.6(8) . . ? N2 C9 C16 117.1(9) . . ? C9 C10 C11 120.1(9) . . ? C13 C11 C10 118.0(10) . . ? C13 C11 C12 124.7(10) . . ? C10 C11 C12 117.3(10) . . ? F9 C12 F8 107.1(11) . . ? F9 C12 F7 104.5(13) . . ? F8 C12 F7 103.8(10) . . ? F9 C12 C11 115.8(10) . . ? F8 C12 C11 111.9(11) . . ? F7 C12 C11 112.8(10) . . ? C14 C13 C11 122.5(9) . . ? C16 C14 C13 118.8(10) . . ? C16 C14 C15 122.3(11) . . ? C13 C14 C15 118.9(9) . . ? F11 C15 F10 104.7(8) . . ? F11 C15 F12 105.5(9) . . ? F10 C15 F12 103.8(9) . . ? F11 C15 C14 112.1(9) . . ? F10 C15 C14 115.3(10) . . ? F12 C15 C14 114.4(9) . . ? C14 C16 C9 122.9(11) . . ? C18 C17 N3 119.9(7) . . ? C18 C17 C24 118.6(7) . . ? N3 C17 C24 121.5(7) . . ? C19 C18 C17 120.2(7) . . ? C18 C19 C21 122.1(8) . . ? C18 C19 C20B 119.2(8) . . ? C21 C19 C20B 118.6(7) . . ? C19 C21 C22 118.2(7) . . ? C24 C22 C21 120.1(7) . . ? C24 C22 C23 118.6(8) . . ? C21 C22 C23 121.3(7) . . ? F17 C23 F18 109.3(8) . . ? F17 C23 F16 106.1(7) . . ? F18 C23 F16 104.3(8) . . ? F17 C23 C22 113.1(8) . . ? F18 C23 C22 111.5(7) . . ? F16 C23 C22 112.0(7) . . ? C22 C24 C17 120.6(7) . . ? F14B C20B F13B 108.5(11) . . ? F14B C20B F15B 102.3(10) . . ? F13B C20B F15B 101.0(11) . . ? F14B C20B C19 120.1(10) . . ? F13B C20B C19 113.8(10) . . ? F15B C20B C19 108.9(9) . . ? O3 C25 O2 124.2(7) . . ? O3 C25 C26 118.4(6) . . ? O2 C25 C26 117.3(7) . . ? C35 N4 C39 110.8(6) . . ? C35 N4 C27 106.7(5) . . ? C39 N4 C27 110.5(6) . . ? C35 N4 C31 111.3(6) . . ? C39 N4 C31 107.0(5) . . ? C27 N4 C31 110.6(6) . . ? C28 C27 N4 115.8(6) . . ? C27 C28 C29 111.6(7) . . ? C28 C29 C30 112.3(7) . . ? C32 C31 N4 116.9(6) . . ? C31 C32 C33 110.3(6) . . ? C34 C33 C32 112.4(7) . . ? N4 C35 C36 115.3(6) . . ? C35 C36 C37 109.5(6) . . ? C38 C37 C36 111.4(7) . . ? N4 C39 C40 115.9(6) . . ? C39 C40 C41 110.9(6) . . ? C42 C41 C40 113.9(8) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.615 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.072 _iucr_refine_instructions_details ; TITL SHELX in P2(1) CELL 0.71073 9.3758 24.9098 10.4327 90.000 92.512 90.000 ZERR 2.00 0.0050 0.0127 0.0052 0.000 0.009 0.000 LATT -1 SYMM - X, 1/2 + Y, - Z SFAC C H N O F P UNIT 84 106 8 8 36 2 MERG 4 SHEL 7 0.84 DFIX 0.84 H1W O1W H2W O1W DFIX 1.4 H1W H2W EADP C20A C20B EADP F13A F13B F14A F14B F15A F15B EXYZ C20A C20B FMAP 2 PLAN 25 SIZE 0.01 0.20 0.20 ACTA 55.00 BUMP 0.02000 WGHT 0.13450 1.14200 L.S. 16 FVAR 3.64265 0.46777 O1W 4 0.016240 0.246997 0.042424 11.00000 0.03554 0.06419 = 0.03543 -0.00468 0.00556 -0.00748 H1W 2 0.070940 0.221078 0.056769 11.00000 -1.50000 H2W 2 -0.056299 0.239477 -0.004155 11.00000 -1.50000 MOLE 1 P1 6 0.359672 0.218252 0.943400 11.00000 0.03335 0.03301 = 0.03264 0.00600 0.00177 -0.00215 O1 4 0.280159 0.190602 1.041705 11.00000 0.03541 0.05462 = 0.04644 0.02470 0.00446 -0.00687 N1 3 0.248193 0.263847 0.877181 11.00000 0.02957 0.03754 = 0.04004 0.00529 0.00452 -0.00442 AFIX 43 H1 2 0.159662 0.259718 0.893190 11.00000 -1.20000 AFIX 0 N2 3 0.424863 0.177661 0.836752 11.00000 0.04495 0.02987 = 0.04399 -0.00255 -0.00509 -0.00447 AFIX 43 H2 2 0.509342 0.185080 0.813086 11.00000 -1.20000 AFIX 0 N3 3 0.507165 0.250495 0.987721 11.00000 0.03181 0.03632 = 0.03112 -0.00105 0.00233 0.00157 AFIX 43 H3 2 0.586867 0.233820 0.981414 11.00000 -1.20000 AFIX 0 C1 1 0.278443 0.307412 0.800025 11.00000 0.03524 0.03024 = 0.02803 0.00077 0.00408 -0.00429 C2 1 0.407027 0.310197 0.734897 11.00000 0.03638 0.02558 = 0.03254 0.00390 0.00242 0.00276 AFIX 43 H2A 2 0.470579 0.281518 0.738698 11.00000 -1.20000 AFIX 0 C3 1 0.438192 0.355433 0.665751 11.00000 0.03817 0.03277 = 0.03632 0.00527 0.00970 0.00491 C4 1 0.577858 0.358787 0.602425 11.00000 0.04595 0.04091 = 0.06167 0.01865 0.02356 0.01468 C5 1 0.344568 0.398018 0.654413 11.00000 0.04740 0.03472 = 0.04255 0.01248 0.01214 0.01324 AFIX 43 H5 2 0.367029 0.428543 0.608098 11.00000 -1.20000 AFIX 0 C6 1 0.216548 0.393917 0.713928 11.00000 0.04298 0.03293 = 0.04679 0.00030 0.00219 0.00175 C7 1 0.113140 0.440221 0.705770 11.00000 0.04761 0.04269 = 0.06403 0.00345 0.01816 0.01267 C8 1 0.184475 0.349881 0.787711 11.00000 0.04350 0.03635 = 0.03078 0.00490 0.00656 0.00476 AFIX 43 H8 2 0.098862 0.348853 0.829416 11.00000 -1.20000 AFIX 0 C9 1 0.359979 0.132317 0.779274 11.00000 0.06412 0.02771 = 0.04217 0.00839 -0.01547 -0.00608 C10 1 0.222523 0.116371 0.794164 11.00000 0.04275 0.04457 = 0.06130 0.00818 -0.00640 0.00372 AFIX 43 H10 2 0.164916 0.135566 0.848205 11.00000 -1.20000 AFIX 0 C11 1 0.166182 0.070276 0.727199 11.00000 0.04706 0.05638 = 0.05608 0.01613 -0.00036 -0.00643 C12 1 0.018055 0.056192 0.745993 11.00000 0.05331 0.06207 = 0.09204 0.00065 0.00106 -0.01253 C13 1 0.255672 0.041613 0.654241 11.00000 0.05790 0.05549 = 0.04479 0.00780 -0.00285 0.00543 AFIX 43 H13 2 0.221176 0.010998 0.612337 11.00000 -1.20000 AFIX 0 C14 1 0.393293 0.056152 0.640564 11.00000 0.06319 0.04402 = 0.05268 0.00425 0.00078 -0.00476 C15 1 0.483959 0.022622 0.559842 11.00000 0.08621 0.04790 = 0.04978 -0.00077 0.00455 0.00793 C16 1 0.443326 0.100819 0.699167 11.00000 0.09618 0.03412 = 0.03506 0.00289 -0.00472 -0.00290 AFIX 43 H16 2 0.536783 0.111342 0.686276 11.00000 -1.20000 AFIX 0 C17 1 0.511956 0.303135 1.034940 11.00000 0.03251 0.04379 = 0.02904 0.00183 -0.00096 0.00244 C18 1 0.628069 0.335541 1.011518 11.00000 0.02893 0.04569 = 0.03262 -0.00209 0.00633 -0.00252 AFIX 43 H18 2 0.704507 0.321862 0.967948 11.00000 -1.20000 AFIX 0 C19 1 0.630063 0.388101 1.052930 11.00000 0.03688 0.04976 = 0.04945 -0.00358 0.01319 -0.00700 C21 1 0.517506 0.410293 1.116321 11.00000 0.04598 0.03921 = 0.05376 -0.01310 0.01373 -0.00302 AFIX 43 H21 2 0.518530 0.446263 1.140225 11.00000 -1.20000 AFIX 0 C22 1 0.402823 0.377315 1.143288 11.00000 0.04400 0.04186 = 0.03365 0.00226 0.00420 -0.00105 C23 1 0.280012 0.397893 1.214616 11.00000 0.03407 0.06186 = 0.04472 -0.00770 0.00791 0.00169 C24 1 0.400247 0.324240 1.104358 11.00000 0.03200 0.04467 = 0.02877 0.00294 0.00017 -0.00192 AFIX 43 H24 2 0.323892 0.302411 1.124373 11.00000 -1.20000 AFIX 0 F1 5 0.680557 0.328522 0.659268 11.00000 0.04264 0.08928 = 0.10544 0.05206 0.03333 0.02259 F2 5 0.566883 0.345661 0.481895 11.00000 0.05478 0.19362 = 0.05925 -0.01663 0.02859 -0.00101 F3 5 0.635550 0.408022 0.605880 11.00000 0.04979 0.05849 = 0.15343 0.02765 0.03514 0.00142 F4 5 0.122450 0.468304 0.599774 11.00000 0.14952 0.11013 = 0.15857 0.09376 0.09667 0.09410 F5 5 0.128453 0.473294 0.801816 11.00000 0.07701 0.05710 = 0.16309 -0.05818 -0.02746 0.02885 F6 5 -0.021802 0.425090 0.704183 11.00000 0.04940 0.05246 = 0.09779 -0.00306 -0.00535 0.01967 F7 5 -0.073724 0.089448 0.684571 11.00000 0.05277 0.10633 = 0.28951 0.06372 -0.02545 0.00120 F8 5 -0.014646 0.008209 0.696925 11.00000 0.09161 0.09792 = 0.19642 -0.04246 0.03425 -0.04853 F9 5 -0.019725 0.056383 0.864082 11.00000 0.08957 0.24749 = 0.11074 -0.05290 0.03383 -0.08077 F10 5 0.438718 0.019154 0.437237 11.00000 0.12275 0.08432 = 0.05185 0.00835 0.00551 0.02037 F11 5 0.491035 -0.028050 0.600527 11.00000 0.11943 0.05232 = 0.06532 0.01611 0.00922 0.00390 F12 5 0.620358 0.039830 0.554555 11.00000 0.07810 0.07529 = 0.13874 -0.04512 0.04177 -0.01340 PART 1 SAME C20B F14B F15B F13B C20B 1 0.754927 0.422602 1.026426 21.00000 0.05540 0.04435 = 0.08719 -0.03172 0.02976 -0.01663 F13B 5 0.861114 0.395887 0.969731 21.00000 0.06343 0.07384 = 0.09971 -0.02086 0.02344 -0.03116 F14B 5 0.736914 0.466779 0.967297 21.00000 0.06343 0.07384 = 0.09971 -0.02086 0.02344 -0.03116 F15B 5 0.824461 0.437437 1.143038 21.00000 0.06343 0.07384 = 0.09971 -0.02086 0.02344 -0.03116 PART 2 SAME C20B > F15B C20A 1 0.754927 0.422602 1.026426 -21.00000 0.05540 0.04435 = 0.08719 -0.03172 0.02976 -0.01663 F13A 5 0.753923 0.471497 1.074572 -21.00000 0.06343 0.07384 = 0.09971 -0.02086 0.02344 -0.03116 F14A 5 0.730173 0.442012 0.898312 -21.00000 0.06343 0.07384 = 0.09971 -0.02086 0.02344 -0.03116 F15A 5 0.875648 0.397835 1.015562 -21.00000 0.06343 0.07384 = 0.09971 -0.02086 0.02344 -0.03116 PART 0 F16 5 0.286008 0.382490 1.337903 11.00000 0.06984 0.06561 = 0.05406 0.00190 0.02794 0.00601 F17 5 0.272597 0.450629 1.215448 11.00000 0.08465 0.05304 = 0.10220 0.01311 0.05382 0.02458 F18 5 0.155681 0.378051 1.167284 11.00000 0.04899 0.14000 = 0.08943 -0.05076 0.01187 0.00583 MOLE 2 O2 4 0.772135 0.220257 0.903505 11.00000 0.03908 0.04982 = 0.02971 0.00083 0.00218 0.00251 O3 4 0.663599 0.203452 0.713529 11.00000 0.03860 0.05064 = 0.03224 -0.00493 -0.00318 0.00206 C25 1 0.772059 0.214717 0.782463 11.00000 0.03509 0.03695 = 0.03488 -0.00541 -0.00120 0.00495 C26 1 0.910286 0.223587 0.718586 11.00000 0.04296 0.06112 = 0.03829 0.00218 0.00618 0.00768 AFIX 137 H26A 2 0.910598 0.203143 0.640594 11.00000 -1.50000 H26B 2 0.988178 0.212267 0.775003 11.00000 -1.50000 H26C 2 0.920583 0.261030 0.699262 11.00000 -1.50000 AFIX 0 MOLE 3 N4 3 0.702886 0.171071 0.298113 11.00000 0.03489 0.03842 = 0.02660 0.00536 0.00449 -0.00101 C27 1 0.828046 0.138320 0.354050 11.00000 0.02993 0.04408 = 0.03416 0.00462 0.00035 0.00186 AFIX 23 H27A 2 0.868819 0.157216 0.428244 11.00000 -1.20000 H27B 2 0.791754 0.104275 0.383851 11.00000 -1.20000 AFIX 0 C28 1 0.944364 0.127274 0.264526 11.00000 0.03965 0.04945 = 0.04375 0.00905 0.00653 -0.00104 AFIX 23 H28A 2 0.981969 0.161003 0.234084 11.00000 -1.20000 H28B 2 0.905640 0.107515 0.190819 11.00000 -1.20000 AFIX 0 C29 1 1.064819 0.094960 0.329933 11.00000 0.04343 0.03876 = 0.05702 0.00758 0.00095 -0.00405 AFIX 23 H29A 2 1.025369 0.062936 0.367666 11.00000 -1.20000 H29B 2 1.109090 0.116199 0.398708 11.00000 -1.20000 AFIX 0 C30 1 1.179392 0.078488 0.236032 11.00000 0.03614 0.06255 = 0.08496 0.02040 0.01706 0.01403 AFIX 137 H30A 2 1.134814 0.060196 0.163864 11.00000 -1.50000 H30B 2 1.247359 0.055043 0.278832 11.00000 -1.50000 H30C 2 1.227386 0.109964 0.206896 11.00000 -1.50000 AFIX 0 C31 1 0.752567 0.226899 0.259599 11.00000 0.04425 0.03075 = 0.03360 0.00317 0.00318 0.00180 AFIX 23 H31A 2 0.818335 0.222838 0.191027 11.00000 -1.20000 H31B 2 0.670287 0.246501 0.224785 11.00000 -1.20000 AFIX 0 C32 1 0.824475 0.260790 0.363708 11.00000 0.02602 0.04359 = 0.04018 -0.00084 0.00138 -0.00024 AFIX 23 H32A 2 0.914874 0.244594 0.390969 11.00000 -1.20000 H32B 2 0.764778 0.262266 0.437248 11.00000 -1.20000 AFIX 0 C33 1 0.850028 0.317295 0.314878 11.00000 0.05036 0.04895 = 0.04025 -0.00984 0.01688 -0.00730 AFIX 23 H33A 2 0.903394 0.315311 0.237441 11.00000 -1.20000 H33B 2 0.758781 0.334008 0.292828 11.00000 -1.20000 AFIX 0 C34 1 0.930301 0.351576 0.411415 11.00000 0.03708 0.05476 = 0.05617 -0.00972 0.01242 -0.00833 AFIX 137 H34A 2 0.878949 0.353103 0.488944 11.00000 -1.50000 H34B 2 0.940243 0.387158 0.377605 11.00000 -1.50000 H34C 2 1.023159 0.336437 0.429569 11.00000 -1.50000 AFIX 0 C35 1 0.594066 0.174108 0.400802 11.00000 0.03295 0.04606 = 0.02870 0.00221 0.00605 0.00415 AFIX 23 H35A 2 0.641085 0.187556 0.479019 11.00000 -1.20000 H35B 2 0.560886 0.138054 0.418109 11.00000 -1.20000 AFIX 0 C36 1 0.465145 0.209281 0.368163 11.00000 0.03731 0.04618 = 0.03129 0.00165 0.00343 0.00444 AFIX 23 H36A 2 0.420005 0.197850 0.287282 11.00000 -1.20000 H36B 2 0.495205 0.246302 0.359203 11.00000 -1.20000 AFIX 0 C37 1 0.358256 0.204957 0.475235 11.00000 0.03413 0.05442 = 0.03375 -0.00251 0.00348 -0.00153 AFIX 23 H37A 2 0.325141 0.168172 0.480757 11.00000 -1.20000 H37B 2 0.405914 0.214176 0.556669 11.00000 -1.20000 AFIX 0 C38 1 0.231047 0.241806 0.451226 11.00000 0.03445 0.07269 = 0.04421 0.00586 0.00612 0.00829 AFIX 137 H38A 2 0.263511 0.278238 0.445348 11.00000 -1.50000 H38B 2 0.167781 0.238669 0.520740 11.00000 -1.50000 H38C 2 0.181352 0.231829 0.372397 11.00000 -1.50000 AFIX 0 C39 1 0.639850 0.144491 0.177232 11.00000 0.03481 0.04018 = 0.02876 -0.00279 -0.00107 0.00510 AFIX 23 H39A 2 0.709657 0.146526 0.111476 11.00000 -1.20000 H39B 2 0.557102 0.165051 0.147229 11.00000 -1.20000 AFIX 0 C40 1 0.594947 0.086110 0.190872 11.00000 0.04210 0.04289 = 0.03453 -0.00307 0.00396 -0.00320 AFIX 23 H40A 2 0.521430 0.083585 0.253181 11.00000 -1.20000 H40B 2 0.676182 0.065041 0.222256 11.00000 -1.20000 AFIX 0 C41 1 0.538220 0.063269 0.062716 11.00000 0.06102 0.04462 = 0.04090 0.00152 -0.00701 -0.00622 AFIX 23 H41A 2 0.497722 0.028079 0.077336 11.00000 -1.20000 H41B 2 0.462075 0.086249 0.028724 11.00000 -1.20000 AFIX 0 C42 1 0.649744 0.058341 -0.035390 11.00000 0.09146 0.04613 = 0.04873 -0.00379 0.00599 0.01425 AFIX 137 H42A 2 0.682840 0.093449 -0.057704 11.00000 -1.50000 H42B 2 0.609377 0.040929 -0.110636 11.00000 -1.50000 H42C 2 0.728393 0.037493 -0.000620 11.00000 -1.50000 AFIX 0 HKLF 4 END ; data_shelx_mel _database_code_depnum_ccdc_archive 'CCDC 910544' #TrackingRef '2012jh0208.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C24 H12 F18 N3 O P, 2(C16 H36 N), 2(Cl), H2 O ' _chemical_formula_sum 'C56 H86 Cl2 F18 N5 O2 P' _chemical_formula_weight 1305.17 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' 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' F F 0.0171 0.0103 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 13.788(8) _cell_length_b 18.964(10) _cell_length_c 25.385(14) _cell_angle_alpha 90.00 _cell_angle_beta 102.004(11) _cell_angle_gamma 90.00 _cell_volume 6492(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 16993 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 31.5 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2736 _exptl_absorpt_coefficient_mu 0.219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9575 _exptl_absorpt_correction_T_max 0.9870 _exptl_absorpt_process_details ; Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_source_power 2.475 _diffrn_source_voltage 45.0 _diffrn_source_current 55.0 _diffrn_source 'Rotating Anode' _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_collimation 'Confocal mirrors, HF Varimax ' _diffrn_detector 'CCD plate' _diffrn_detector_type 'Rigaku HG Saturn724+ (2x2 bin mode)' _diffrn_detector_area_resol_mean 28.5714 _diffrn_measurement_device 'four-circle \k diffractometer' _diffrn_measurement_device_type 'Rigaku AFC12 (Right)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support 'MiTeGen MicroMesh' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 43186 _diffrn_reflns_av_R_equivalents 0.0920 _diffrn_reflns_av_sigmaI/netI 0.1279 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 27.49 _reflns_number_total 14776 _reflns_number_gt 8446 _reflns_threshold_expression >2\s(I) _computing_data_collection ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; Images generated using CrystalMaker: a crystal and molecular structures program for Mac and Windows. CrystalMaker Software Ltd, Oxford, England (www.crystalmaker.com) ; _computing_publication_material 'WINGX (Farrugia, 1998)' _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^ > 2\s(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^)+(0.0946P)^2^+12.2290P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 14776 _refine_ls_number_parameters 769 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.2162 _refine_ls_R_factor_gt 0.1408 _refine_ls_wR_factor_ref 0.3210 _refine_ls_wR_factor_gt 0.2774 _refine_ls_goodness_of_fit_ref 1.147 _refine_ls_restrained_S_all 1.148 _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 O1W O -0.3912(3) 0.4464(2) 0.0756(2) 0.0897(15) Uani 1 1 d D . . H1W H -0.3510(17) 0.430(2) 0.0567(12) 0.135 Uiso 1 1 d D . . H2W H -0.418(3) 0.4112(16) 0.0889(18) 0.135 Uiso 1 1 d D . . N4 N 0.3242(3) 0.1264(2) 0.07680(16) 0.0506(11) Uani 1 1 d . . . C1 C 0.3106(4) 0.1670(3) 0.0241(2) 0.0548(14) Uani 1 1 d . . . H1A H 0.2494 0.1936 0.0195 0.066 Uiso 1 1 calc R . . H1B H 0.3645 0.2006 0.0269 0.066 Uiso 1 1 calc R . . C2 C 0.3075(5) 0.1229(3) -0.0254(2) 0.0703(18) Uani 1 1 d . . . H2A H 0.2537 0.0891 -0.0294 0.084 Uiso 1 1 calc R . . H2B H 0.3692 0.0972 -0.0225 0.084 Uiso 1 1 calc R . . C3 C 0.2919(6) 0.1726(4) -0.0748(2) 0.087(2) Uani 1 1 d . . . H3A H 0.2286 0.1965 -0.0781 0.104 Uiso 1 1 calc R . . H3B H 0.3434 0.2082 -0.0689 0.104 Uiso 1 1 calc R . . C4 C 0.2934(7) 0.1357(4) -0.1247(3) 0.117(3) Uani 1 1 d . . . H4A H 0.3589 0.1178 -0.1237 0.176 Uiso 1 1 calc R . . H4B H 0.2752 0.1676 -0.1544 0.176 Uiso 1 1 calc R . . H4C H 0.2472 0.0972 -0.1288 0.176 Uiso 1 1 calc R . . C5 C 0.4160(4) 0.0798(3) 0.0850(2) 0.0562(15) Uani 1 1 d . . . H5A H 0.4211 0.0548 0.1187 0.067 Uiso 1 1 calc R . . H5B H 0.4060 0.0449 0.0564 0.067 Uiso 1 1 calc R . . C6 C 0.5132(4) 0.1158(3) 0.0858(3) 0.0712(18) Uani 1 1 d . . . H6A H 0.5305 0.1455 0.1175 0.085 Uiso 1 1 calc R . . H6B H 0.5082 0.1454 0.0542 0.085 Uiso 1 1 calc R . . C7 C 0.5934(4) 0.0593(3) 0.0866(3) 0.0741(19) Uani 1 1 d . . . H7A H 0.5941 0.0284 0.1171 0.089 Uiso 1 1 calc R . . H7B H 0.5755 0.0311 0.0541 0.089 Uiso 1 1 calc R . . C8 C 0.6925(5) 0.0870(4) 0.0899(3) 0.085(2) Uani 1 1 d . . . H8A H 0.6912 0.1220 0.0625 0.128 Uiso 1 1 calc R . . H8B H 0.7361 0.0493 0.0847 0.128 Uiso 1 1 calc R . . H8C H 0.7158 0.1078 0.1247 0.128 Uiso 1 1 calc R . . C9 C 0.2386(4) 0.0771(3) 0.0790(2) 0.0498(13) Uani 1 1 d . . . H9A H 0.2394 0.0397 0.0531 0.060 Uiso 1 1 calc R . . H9B H 0.2508 0.0556 0.1144 0.060 Uiso 1 1 calc R . . C10 C 0.1357(4) 0.1086(2) 0.0682(2) 0.0474(13) Uani 1 1 d . . . H10A H 0.1183 0.1258 0.0315 0.057 Uiso 1 1 calc R . . H10B H 0.1335 0.1480 0.0924 0.057 Uiso 1 1 calc R . . C11 C 0.0624(4) 0.0514(3) 0.0772(2) 0.0550(14) Uani 1 1 d . . . H11A H 0.0684 0.0115 0.0542 0.066 Uiso 1 1 calc R . . H11B H 0.0806 0.0354 0.1143 0.066 Uiso 1 1 calc R . . C12 C -0.0444(4) 0.0753(3) 0.0660(2) 0.0630(16) Uani 1 1 d . . . H12A H -0.0506 0.1163 0.0872 0.095 Uiso 1 1 calc R . . H12B H -0.0853 0.0382 0.0752 0.095 Uiso 1 1 calc R . . H12C H -0.0654 0.0865 0.0285 0.095 Uiso 1 1 calc R . . C13 C 0.3329(4) 0.1846(3) 0.1195(2) 0.0519(14) Uani 1 1 d . . . H13A H 0.3890 0.2142 0.1166 0.062 Uiso 1 1 calc R . . H13B H 0.2739 0.2137 0.1108 0.062 Uiso 1 1 calc R . . C14 C 0.3455(4) 0.1609(3) 0.1770(2) 0.0653(17) Uani 1 1 d . . . H14A H 0.4024 0.1298 0.1864 0.078 Uiso 1 1 calc R . . H14B H 0.2871 0.1354 0.1820 0.078 Uiso 1 1 calc R . . C15 C 0.3609(5) 0.2266(3) 0.2131(2) 0.0710(18) Uani 1 1 d . . . H15A H 0.4185 0.2520 0.2069 0.085 Uiso 1 1 calc R . . H15B H 0.3039 0.2573 0.2027 0.085 Uiso 1 1 calc R . . C16 C 0.3750(6) 0.2110(4) 0.2716(3) 0.101(3) Uani 1 1 d . . . H16A H 0.3176 0.1868 0.2784 0.152 Uiso 1 1 calc R . . H16B H 0.3839 0.2543 0.2916 0.152 Uiso 1 1 calc R . . H16C H 0.4325 0.1817 0.2826 0.152 Uiso 1 1 calc R . . N5 N -0.3121(3) 0.5124(2) -0.09045(16) 0.0530(12) Uani 1 1 d . . . C17 C -0.4001(4) 0.4708(3) -0.0794(2) 0.0671(18) Uani 1 1 d . . . H17A H -0.3863 0.4581 -0.0415 0.081 Uiso 1 1 calc R . . H17B H -0.4576 0.5016 -0.0857 0.081 Uiso 1 1 calc R . . C18 C -0.4274(4) 0.4039(4) -0.1122(3) 0.083(2) Uani 1 1 d . . . H18A H -0.3718 0.3714 -0.1054 0.099 Uiso 1 1 calc R . . H18B H -0.4420 0.4153 -0.1503 0.099 Uiso 1 1 calc R . . C19 C -0.5190(5) 0.3686(5) -0.0967(3) 0.117(3) Uani 1 1 d . . . H19A H -0.5709 0.4037 -0.0991 0.140 Uiso 1 1 calc R . . H19B H -0.5434 0.3321 -0.1230 0.140 Uiso 1 1 calc R . . C20 C -0.5023(6) 0.3393(5) -0.0467(4) 0.150(4) Uani 1 1 d . . . H20A H -0.4449 0.3094 -0.0419 0.225 Uiso 1 1 calc R . . H20B H -0.5588 0.3118 -0.0428 0.225 Uiso 1 1 calc R . . H20C H -0.4912 0.3759 -0.0200 0.225 Uiso 1 1 calc R . . C21 C -0.2977(3) 0.5773(3) -0.0551(2) 0.0494(13) Uani 1 1 d . . . H21A H -0.3587 0.6043 -0.0626 0.059 Uiso 1 1 calc R . . H21B H -0.2466 0.6061 -0.0655 0.059 Uiso 1 1 calc R . . C22 C -0.2690(4) 0.5647(3) 0.0058(2) 0.0580(15) Uani 1 1 d . . . H22A H -0.3252 0.5449 0.0182 0.070 Uiso 1 1 calc R . . H22B H -0.2151 0.5309 0.0135 0.070 Uiso 1 1 calc R . . C23 C -0.2378(4) 0.6319(3) 0.0354(2) 0.0639(16) Uani 1 1 d . . . H23A H -0.2907 0.6663 0.0262 0.077 Uiso 1 1 calc R . . H23B H -0.1799 0.6505 0.0240 0.077 Uiso 1 1 calc R . . C24 C -0.2130(5) 0.6217(4) 0.0970(2) 0.0761(19) Uani 1 1 d . . . H24A H -0.2716 0.6074 0.1090 0.114 Uiso 1 1 calc R . . H24B H -0.1889 0.6653 0.1141 0.114 Uiso 1 1 calc R . . H24C H -0.1629 0.5860 0.1062 0.114 Uiso 1 1 calc R . . C25 C -0.2235(3) 0.4649(3) -0.07812(19) 0.0490(13) Uani 1 1 d . . . H25A H -0.2331 0.4270 -0.1044 0.059 Uiso 1 1 calc R . . H25B H -0.2209 0.4438 -0.0430 0.059 Uiso 1 1 calc R . . C26 C -0.1232(3) 0.4992(3) -0.07794(19) 0.0448(12) Uani 1 1 d . . . H26A H -0.1126 0.5379 -0.0524 0.054 Uiso 1 1 calc R . . H26B H -0.1228 0.5182 -0.1134 0.054 Uiso 1 1 calc R . . C27 C -0.0397(4) 0.4452(3) -0.0626(2) 0.0604(16) Uani 1 1 d . . . H27A H 0.0230 0.4693 -0.0608 0.073 Uiso 1 1 calc R . . H27B H -0.0404 0.4277 -0.0268 0.073 Uiso 1 1 calc R . . C28 C -0.0436(5) 0.3831(3) -0.0998(3) 0.085(2) Uani 1 1 d . . . H28A H -0.1038 0.3572 -0.1007 0.128 Uiso 1 1 calc R . . H28B H 0.0123 0.3530 -0.0871 0.128 Uiso 1 1 calc R . . H28C H -0.0419 0.3994 -0.1354 0.128 Uiso 1 1 calc R . . C29 C -0.3277(4) 0.5350(4) -0.1500(2) 0.0659(17) Uani 1 1 d . . . H29A H -0.2750 0.5673 -0.1536 0.079 Uiso 1 1 calc R . . H29B H -0.3210 0.4936 -0.1714 0.079 Uiso 1 1 calc R . . C30 C -0.4224(4) 0.5686(4) -0.1728(2) 0.077(2) Uani 1 1 d . . . H30A H -0.4284 0.6123 -0.1538 0.093 Uiso 1 1 calc R . . H30B H -0.4764 0.5378 -0.1686 0.093 Uiso 1 1 calc R . . C31 C -0.4284(5) 0.5840(3) -0.2336(2) 0.0705(18) Uani 1 1 d . . . H31A H -0.4818 0.6174 -0.2454 0.085 Uiso 1 1 calc R . . H31B H -0.3672 0.6069 -0.2372 0.085 Uiso 1 1 calc R . . C32 C -0.4448(5) 0.5219(3) -0.2709(2) 0.0744(19) Uani 1 1 d . . . H32A H -0.3878 0.4916 -0.2632 0.112 Uiso 1 1 calc R . . H32B H -0.4546 0.5381 -0.3075 0.112 Uiso 1 1 calc R . . H32C H -0.5023 0.4964 -0.2659 0.112 Uiso 1 1 calc R . . P1 P -0.18203(8) 0.33185(7) 0.06247(5) 0.0365(3) Uani 1 1 d . . . O1 O -0.2567(2) 0.37146(18) 0.02402(12) 0.0501(9) Uani 1 1 d . . . N1 N -0.1153(3) 0.2784(2) 0.03362(13) 0.0379(9) Uani 1 1 d . . . H1 H -0.0534 0.2758 0.0485 0.045 Uiso 1 1 calc R . . N2 N -0.2390(3) 0.28954(19) 0.10363(14) 0.0386(9) Uani 1 1 d . . . H2 H -0.3023 0.2862 0.0933 0.046 Uiso 1 1 calc R . . N3 N -0.0899(2) 0.37593(18) 0.10003(13) 0.0331(8) Uani 1 1 d . . . H3 H -0.0353 0.3765 0.0888 0.040 Uiso 1 1 calc R . . C33 C -0.1461(3) 0.2366(2) -0.01191(17) 0.0385(11) Uani 1 1 d . B . C34 C -0.0773(4) 0.2149(2) -0.04125(18) 0.0459(13) Uani 1 1 d . . . H34 H -0.0115 0.2288 -0.0304 0.055 Uiso 1 1 calc R . . C35 C -0.1045(5) 0.1734(3) -0.0860(2) 0.0563(15) Uani 1 1 d . B . C36 C -0.0268(5) 0.1520(3) -0.1167(2) 0.0708(18) Uani 1 1 d . . . C37 C -0.1999(5) 0.1503(3) -0.1024(2) 0.0641(18) Uani 1 1 d . . . H37 H -0.2174 0.1210 -0.1322 0.077 Uiso 1 1 calc R A 1 C38A C -0.2715(4) 0.1715(3) -0.0732(2) 0.0596(16) Uani 0.515(4) 1 d P B 1 C39A C -0.3771(4) 0.1474(3) -0.0881(2) 0.096(3) Uani 0.515(4) 1 d P B 1 F4A F -0.3796(6) 0.0972(4) -0.1328(3) 0.0976(12) Uani 0.515(4) 1 d P B 1 F5A F -0.4293(6) 0.1995(5) -0.1134(3) 0.0976(12) Uani 0.515(4) 1 d P B 1 F6A F -0.4034(6) 0.1097(5) -0.0548(3) 0.0976(12) Uani 0.515(4) 1 d P B 1 C38B C -0.2715(4) 0.1715(3) -0.0732(2) 0.0596(16) Uani 0.485(4) 1 d PD B 2 C39B C -0.3771(4) 0.1474(3) -0.0881(2) 0.096(3) Uani 0.485(4) 1 d PD B 2 F4B F -0.4321(5) 0.1596(5) -0.0488(3) 0.0976(12) Uani 0.485(4) 1 d PD B 2 F5B F -0.3871(6) 0.0778(3) -0.0945(3) 0.0976(12) Uani 0.485(4) 1 d PD B 2 F6B F -0.4335(6) 0.1742(4) -0.1316(3) 0.0976(12) Uani 0.485(4) 1 d PD B 2 C40 C -0.2448(4) 0.2148(2) -0.0281(2) 0.0481(13) Uani 1 1 d . . . H40 H -0.2921 0.2291 -0.0090 0.058 Uiso 1 1 calc R B 1 C41 C -0.1988(3) 0.2582(2) 0.15316(17) 0.0369(11) Uani 1 1 d . . . C42 C -0.0987(3) 0.2400(2) 0.16767(18) 0.0393(11) Uani 1 1 d . . . H42 H -0.0567 0.2462 0.1437 0.047 Uiso 1 1 calc R . . C43 C -0.0632(3) 0.2123(2) 0.21892(17) 0.0423(12) Uani 1 1 d D . . C44 C 0.0456(4) 0.1976(3) 0.23498(19) 0.0632(16) Uani 1 1 d D . . F7 F 0.0779(2) 0.15809(18) 0.19714(12) 0.0717(10) Uani 1 1 d D . . F8 F 0.0696(3) 0.1600(2) 0.28029(13) 0.0899(12) Uani 1 1 d D . . F9 F 0.1018(3) 0.25456(19) 0.24111(16) 0.0874(12) Uani 1 1 d D . . C45 C -0.1246(4) 0.2012(3) 0.25481(19) 0.0557(15) Uani 1 1 d . . . H45 H -0.0995 0.1826 0.2888 0.067 Uiso 1 1 calc R . . C46 C -0.2241(4) 0.2181(3) 0.2392(2) 0.0524(14) Uani 1 1 d . . . C47 C -0.2945(5) 0.2058(4) 0.2756(2) 0.0752(19) Uani 1 1 d . . . C48 C -0.2609(4) 0.2470(3) 0.1896(2) 0.0486(13) Uani 1 1 d . . . H48 H -0.3276 0.2592 0.1800 0.058 Uiso 1 1 calc R . . C49 C -0.0896(3) 0.4128(2) 0.14822(18) 0.0380(11) Uani 1 1 d . . . C50 C -0.1753(4) 0.4347(2) 0.16417(18) 0.0445(12) Uani 1 1 d . . . H50 H -0.2373 0.4269 0.1422 0.053 Uiso 1 1 calc R . . C51 C -0.1667(4) 0.4689(2) 0.21383(19) 0.0463(12) Uani 1 1 d . . . C52 C -0.2594(5) 0.4868(3) 0.2313(2) 0.0669(17) Uani 1 1 d . . . C53 C -0.0753(4) 0.4837(3) 0.2458(2) 0.0512(14) Uani 1 1 d . . . H53 H -0.0707 0.5079 0.2781 0.061 Uiso 1 1 calc R . . C54 C 0.0084(4) 0.4625(3) 0.22941(19) 0.0463(13) Uani 1 1 d . . . C55 C 0.1095(5) 0.4802(3) 0.2620(2) 0.0677(18) Uani 1 1 d . . . C56 C 0.0033(4) 0.4256(2) 0.18195(18) 0.0408(11) Uani 1 1 d . . . H56 H 0.0609 0.4094 0.1724 0.049 Uiso 1 1 calc R . . F1 F 0.0210(3) 0.20785(18) -0.13061(13) 0.0845(11) Uani 1 1 d . . . F2 F 0.0452(3) 0.11136(19) -0.08624(15) 0.0912(12) Uani 1 1 d . . . F3 F -0.0614(4) 0.1165(3) -0.16053(17) 0.1338(18) Uani 1 1 d . . . F10 F -0.2508(4) 0.1908(3) 0.32487(16) 0.1403(19) Uani 1 1 d . . . F11 F -0.3553(4) 0.1541(3) 0.25953(19) 0.1658(17) Uani 1 1 d . . . F12 F -0.3494(3) 0.2600(2) 0.28088(16) 0.1132(14) Uani 1 1 d . . . F13 F -0.3209(3) 0.4336(3) 0.2284(2) 0.1277(16) Uani 1 1 d . . . F14 F -0.3086(3) 0.5378(3) 0.20599(18) 0.1566(17) Uani 1 1 d . . . F15 F -0.2446(3) 0.5038(3) 0.28361(15) 0.1110(15) Uani 1 1 d . . . F16 F 0.1729(3) 0.4267(2) 0.26537(17) 0.1095(15) Uani 1 1 d . . . F17 F 0.1084(3) 0.5017(3) 0.31070(14) 0.1050(14) Uani 1 1 d . . . F18 F 0.1544(3) 0.5308(2) 0.23887(16) 0.0979(13) Uani 1 1 d . . . Cl1 Cl 0.10885(8) 0.30097(6) 0.08544(5) 0.0491(3) Uani 1 1 d . . . Cl2 Cl -0.47548(10) 0.29918(9) 0.09135(8) 0.0830(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1W 0.064(3) 0.082(3) 0.127(4) 0.011(3) 0.028(3) 0.013(2) N4 0.054(2) 0.048(2) 0.051(2) 0.006(2) 0.014(2) 0.014(2) C1 0.055(3) 0.052(3) 0.058(3) 0.016(3) 0.014(2) 0.014(3) C2 0.086(4) 0.071(4) 0.052(3) 0.010(3) 0.010(3) 0.011(3) C3 0.111(5) 0.085(5) 0.059(4) 0.012(4) 0.008(4) -0.016(4) C4 0.182(9) 0.097(6) 0.072(5) -0.005(4) 0.025(5) -0.027(6) C5 0.057(3) 0.058(3) 0.056(3) 0.008(3) 0.016(2) 0.020(3) C6 0.059(3) 0.064(4) 0.092(4) 0.007(3) 0.019(3) 0.027(3) C7 0.062(4) 0.079(4) 0.082(4) 0.016(4) 0.017(3) 0.010(3) C8 0.060(4) 0.077(5) 0.117(6) 0.006(4) 0.014(4) 0.000(4) C9 0.061(3) 0.038(3) 0.050(3) -0.003(2) 0.011(2) 0.004(2) C10 0.058(3) 0.036(3) 0.050(3) 0.003(2) 0.015(2) 0.001(2) C11 0.067(3) 0.037(3) 0.062(3) -0.001(2) 0.014(3) -0.002(3) C12 0.078(4) 0.048(3) 0.066(3) 0.007(3) 0.020(3) 0.001(3) C13 0.042(3) 0.047(3) 0.066(3) -0.007(3) 0.009(2) 0.005(2) C14 0.062(3) 0.073(4) 0.058(3) -0.007(3) 0.007(3) 0.017(3) C15 0.071(4) 0.078(4) 0.061(4) -0.017(3) 0.006(3) 0.013(3) C16 0.106(6) 0.106(6) 0.088(5) -0.009(5) 0.010(4) 0.020(5) N5 0.037(2) 0.074(3) 0.048(2) 0.009(2) 0.0091(18) -0.010(2) C17 0.042(3) 0.096(5) 0.063(3) 0.004(3) 0.009(3) -0.015(3) C18 0.045(3) 0.097(5) 0.108(5) -0.014(4) 0.020(3) -0.018(3) C19 0.059(4) 0.164(8) 0.119(6) 0.030(6) 0.001(4) -0.009(5) C20 0.077(5) 0.166(9) 0.204(10) 0.088(8) 0.021(6) -0.019(6) C21 0.029(2) 0.061(3) 0.059(3) 0.016(3) 0.011(2) 0.005(2) C22 0.059(3) 0.063(4) 0.058(3) 0.008(3) 0.026(3) 0.005(3) C23 0.068(4) 0.061(4) 0.063(3) 0.003(3) 0.013(3) 0.006(3) C24 0.087(4) 0.085(5) 0.061(4) -0.005(3) 0.025(3) 0.009(4) C25 0.041(2) 0.067(3) 0.039(3) 0.001(2) 0.006(2) -0.015(2) C26 0.038(2) 0.056(3) 0.041(3) -0.005(2) 0.011(2) -0.004(2) C27 0.040(3) 0.077(4) 0.062(3) -0.018(3) 0.007(2) -0.003(3) C28 0.082(5) 0.069(4) 0.099(5) -0.020(4) 0.006(4) -0.003(4) C29 0.044(3) 0.099(5) 0.055(3) 0.022(3) 0.010(2) -0.008(3) C30 0.057(4) 0.096(5) 0.073(4) 0.001(4) -0.001(3) -0.003(4) C31 0.073(4) 0.079(4) 0.053(3) 0.004(3) -0.001(3) -0.008(3) C32 0.075(4) 0.070(4) 0.067(4) 0.004(3) -0.010(3) 0.015(3) P1 0.0322(5) 0.0414(6) 0.0351(6) 0.0053(5) 0.0055(5) 0.0063(5) O1 0.0464(18) 0.059(2) 0.0437(18) 0.0153(16) 0.0075(15) 0.0182(17) N1 0.0309(18) 0.049(2) 0.0309(18) -0.0073(17) 0.0004(15) 0.0055(17) N2 0.0305(17) 0.046(2) 0.0378(19) 0.0039(18) 0.0046(15) -0.0031(17) N3 0.0326(17) 0.0329(19) 0.0357(18) -0.0015(16) 0.0112(15) -0.0007(16) C33 0.044(2) 0.037(2) 0.031(2) 0.007(2) 0.0018(19) 0.000(2) C34 0.063(3) 0.040(3) 0.034(2) -0.002(2) 0.009(2) -0.007(2) C35 0.086(4) 0.041(3) 0.039(3) -0.004(2) 0.006(3) -0.004(3) C36 0.104(5) 0.064(4) 0.044(3) -0.014(3) 0.016(3) -0.006(4) C37 0.110(5) 0.033(3) 0.042(3) -0.001(2) -0.002(3) 0.006(3) C38A 0.067(3) 0.040(3) 0.059(3) 0.008(3) -0.017(3) -0.009(3) C39A 0.121(6) 0.060(4) 0.079(5) -0.001(4) -0.045(4) -0.009(4) F4A 0.0833(19) 0.109(3) 0.087(2) -0.005(2) -0.014(2) -0.032(2) F5A 0.0833(19) 0.109(3) 0.087(2) -0.005(2) -0.014(2) -0.032(2) F6A 0.0833(19) 0.109(3) 0.087(2) -0.005(2) -0.014(2) -0.032(2) C38B 0.067(3) 0.040(3) 0.059(3) 0.008(3) -0.017(3) -0.009(3) C39B 0.121(6) 0.060(4) 0.079(5) -0.001(4) -0.045(4) -0.009(4) F4B 0.0833(19) 0.109(3) 0.087(2) -0.005(2) -0.014(2) -0.032(2) F5B 0.0833(19) 0.109(3) 0.087(2) -0.005(2) -0.014(2) -0.032(2) F6B 0.0833(19) 0.109(3) 0.087(2) -0.005(2) -0.014(2) -0.032(2) C40 0.056(3) 0.037(3) 0.046(3) 0.005(2) -0.002(2) -0.001(2) C41 0.050(2) 0.026(2) 0.035(2) -0.0021(19) 0.009(2) -0.008(2) C42 0.049(3) 0.034(2) 0.037(2) -0.002(2) 0.013(2) -0.001(2) C43 0.062(3) 0.027(2) 0.035(2) 0.0003(19) 0.004(2) 0.000(2) C44 0.068(4) 0.069(4) 0.048(3) 0.009(3) 0.002(3) 0.016(3) F7 0.0633(19) 0.086(2) 0.0615(19) 0.0030(18) 0.0022(16) 0.0305(18) F8 0.102(3) 0.106(3) 0.0551(19) 0.0342(19) 0.0012(18) 0.039(2) F9 0.057(2) 0.073(2) 0.116(3) 0.004(2) -0.019(2) 0.0004(19) C45 0.090(4) 0.043(3) 0.033(2) 0.016(2) 0.012(3) -0.004(3) C46 0.073(3) 0.045(3) 0.041(3) 0.007(2) 0.018(2) -0.006(3) C47 0.105(4) 0.078(4) 0.054(3) 0.023(3) 0.043(3) 0.000(4) C48 0.057(3) 0.038(3) 0.057(3) -0.009(2) 0.025(2) -0.010(2) C49 0.049(2) 0.026(2) 0.041(2) 0.0065(19) 0.015(2) 0.006(2) C50 0.052(3) 0.040(3) 0.042(3) 0.007(2) 0.011(2) 0.007(2) C51 0.065(3) 0.034(3) 0.044(3) 0.008(2) 0.022(2) 0.016(2) C52 0.079(4) 0.076(4) 0.049(3) 0.002(3) 0.023(3) 0.025(3) C53 0.079(4) 0.035(3) 0.039(3) 0.004(2) 0.012(3) 0.008(3) C54 0.061(3) 0.035(3) 0.042(3) 0.005(2) 0.010(2) 0.002(2) C55 0.075(4) 0.063(4) 0.059(4) -0.011(3) 0.001(3) 0.005(3) C56 0.048(3) 0.033(2) 0.044(3) 0.005(2) 0.014(2) 0.001(2) F1 0.137(3) 0.058(2) 0.075(2) 0.0038(17) 0.061(2) 0.007(2) F2 0.121(3) 0.069(2) 0.097(3) 0.014(2) 0.053(2) 0.029(2) F3 0.167(4) 0.146(4) 0.096(3) -0.080(3) 0.047(3) -0.023(3) F10 0.139(3) 0.219(5) 0.078(2) 0.061(3) 0.059(2) 0.026(4) F11 0.251(4) 0.135(3) 0.163(3) -0.069(3) 0.162(3) -0.124(3) F12 0.150(3) 0.105(3) 0.115(3) 0.019(2) 0.098(2) 0.016(3) F13 0.084(2) 0.143(4) 0.179(4) -0.062(3) 0.081(2) -0.012(3) F14 0.160(3) 0.202(4) 0.134(3) 0.090(3) 0.090(3) 0.142(3) F15 0.099(3) 0.168(4) 0.073(2) -0.035(3) 0.034(2) 0.033(3) F16 0.091(3) 0.099(3) 0.115(3) -0.030(3) -0.035(2) 0.016(2) F17 0.093(3) 0.160(4) 0.057(2) -0.042(2) 0.0030(19) -0.024(3) F18 0.083(2) 0.107(3) 0.099(3) 0.003(2) 0.007(2) -0.038(2) Cl1 0.0340(5) 0.0424(6) 0.0719(8) -0.0074(6) 0.0133(5) -0.0005(5) Cl2 0.0437(7) 0.0733(10) 0.1394(14) 0.0270(10) 0.0361(8) 0.0063(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N4 C9 1.515(6) . ? N4 C1 1.520(6) . ? N4 C5 1.521(6) . ? N4 C13 1.533(6) . ? C1 C2 1.504(7) . ? C2 C3 1.546(8) . ? C3 C4 1.451(9) . ? C5 C6 1.500(8) . ? C6 C7 1.537(8) . ? C7 C8 1.449(8) . ? C9 C10 1.511(7) . ? C10 C11 1.532(7) . ? C11 C12 1.511(7) . ? C13 C14 1.504(7) . ? C14 C15 1.535(8) . ? C15 C16 1.487(9) . ? N5 C25 1.498(6) . ? N5 C21 1.510(7) . ? N5 C17 1.522(7) . ? N5 C29 1.542(6) . ? C17 C18 1.521(9) . ? C18 C19 1.551(9) . ? C19 C20 1.363(11) . ? C21 C22 1.533(7) . ? C22 C23 1.498(8) . ? C23 C24 1.541(8) . ? C25 C26 1.527(6) . ? C26 C27 1.529(7) . ? C27 C28 1.505(8) . ? C29 C30 1.459(8) . ? C30 C31 1.556(8) . ? C31 C32 1.499(8) . ? P1 O1 1.469(3) . ? P1 N1 1.641(4) . ? P1 N2 1.642(4) . ? P1 N3 1.648(4) . ? N1 C33 1.393(5) . ? N2 C41 1.397(5) . ? N3 C49 1.408(5) . ? C33 C34 1.385(7) . ? C33 C40 1.399(7) . ? C34 C35 1.370(7) . ? C35 C37 1.367(8) . ? C35 C36 1.504(9) . ? C36 F3 1.303(7) . ? C36 F1 1.334(7) . ? C36 F2 1.363(7) . ? C37 C38A 1.409(8) . ? C38A C40 1.395(7) . ? C38A C39A 1.498(7) . ? C39A F6A 1.220(10) . ? C39A F5A 1.309(10) . ? C39A F4A 1.477(10) . ? C41 C42 1.397(6) . ? C41 C48 1.400(6) . ? C42 C43 1.394(6) . ? C43 C45 1.384(7) . ? C43 C44 1.497(6) . ? C44 F9 1.320(6) . ? C44 F8 1.335(5) . ? C44 F7 1.364(6) . ? C45 C46 1.384(8) . ? C46 C48 1.371(7) . ? C46 C47 1.490(8) . ? C47 F11 1.299(8) . ? C47 F12 1.300(7) . ? C47 F10 1.302(7) . ? C49 C50 1.391(6) . ? C49 C56 1.406(6) . ? C50 C51 1.400(7) . ? C51 C53 1.379(7) . ? C51 C52 1.476(8) . ? C52 F14 1.275(7) . ? C52 F13 1.311(7) . ? C52 F15 1.342(6) . ? C53 C54 1.367(7) . ? C54 C56 1.382(6) . ? C54 C55 1.502(8) . ? C55 F17 1.305(7) . ? C55 F16 1.330(7) . ? C55 F18 1.342(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 N4 C1 113.0(4) . . ? C9 N4 C5 105.6(4) . . ? C1 N4 C5 111.1(4) . . ? C9 N4 C13 111.4(4) . . ? C1 N4 C13 103.5(4) . . ? C5 N4 C13 112.4(4) . . ? C2 C1 N4 115.6(4) . . ? C1 C2 C3 108.3(5) . . ? C4 C3 C2 112.8(6) . . ? C6 C5 N4 117.0(4) . . ? C5 C6 C7 108.7(5) . . ? C8 C7 C6 114.6(6) . . ? C10 C9 N4 117.3(4) . . ? C9 C10 C11 108.5(4) . . ? C12 C11 C10 114.0(4) . . ? C14 C13 N4 116.6(4) . . ? C13 C14 C15 108.2(5) . . ? C16 C15 C14 114.1(6) . . ? C25 N5 C21 111.4(4) . . ? C25 N5 C17 107.2(4) . . ? C21 N5 C17 108.9(4) . . ? C25 N5 C29 108.3(4) . . ? C21 N5 C29 109.3(4) . . ? C17 N5 C29 111.8(4) . . ? C18 C17 N5 116.6(5) . . ? C17 C18 C19 110.0(6) . . ? C20 C19 C18 115.0(7) . . ? N5 C21 C22 116.5(4) . . ? C23 C22 C21 111.2(4) . . ? C22 C23 C24 112.5(5) . . ? N5 C25 C26 116.3(4) . . ? C25 C26 C27 110.4(4) . . ? C28 C27 C26 116.0(5) . . ? C30 C29 N5 116.1(5) . . ? C29 C30 C31 109.5(5) . . ? C32 C31 C30 116.7(5) . . ? O1 P1 N1 113.60(19) . . ? O1 P1 N2 108.10(19) . . ? N1 P1 N2 111.7(2) . . ? O1 P1 N3 118.3(2) . . ? N1 P1 N3 97.79(18) . . ? N2 P1 N3 107.02(18) . . ? C33 N1 P1 128.3(3) . . ? C41 N2 P1 128.9(3) . . ? C49 N3 P1 128.1(3) . . ? C34 C33 N1 119.4(4) . . ? C34 C33 C40 119.2(4) . . ? N1 C33 C40 121.5(4) . . ? C35 C34 C33 121.2(5) . . ? C37 C35 C34 121.0(6) . . ? C37 C35 C36 120.1(5) . . ? C34 C35 C36 118.9(5) . . ? F3 C36 F1 107.3(5) . . ? F3 C36 F2 106.6(5) . . ? F1 C36 F2 104.9(5) . . ? F3 C36 C35 114.0(6) . . ? F1 C36 C35 111.5(5) . . ? F2 C36 C35 111.8(5) . . ? C35 C37 C38A 119.0(5) . . ? C40 C38A C37 120.3(5) . . ? C40 C38A C39A 117.6(5) . . ? C37 C38A C39A 122.0(5) . . ? F6A C39A F5A 124.8(8) . . ? F6A C39A F4A 101.0(6) . . ? F5A C39A F4A 100.8(6) . . ? F6A C39A C38A 114.7(6) . . ? F5A C39A C38A 107.4(6) . . ? F4A C39A C38A 104.9(6) . . ? C38A C40 C33 119.3(5) . . ? N2 C41 C42 121.9(4) . . ? N2 C41 C48 118.5(4) . . ? C42 C41 C48 119.6(4) . . ? C43 C42 C41 118.4(4) . . ? C45 C43 C42 121.9(4) . . ? C45 C43 C44 120.6(4) . . ? C42 C43 C44 117.5(4) . . ? F9 C44 F8 107.6(4) . . ? F9 C44 F7 105.2(4) . . ? F8 C44 F7 104.8(4) . . ? F9 C44 C43 114.2(4) . . ? F8 C44 C43 112.9(4) . . ? F7 C44 C43 111.5(4) . . ? C43 C45 C46 118.9(4) . . ? C48 C46 C45 120.7(5) . . ? C48 C46 C47 117.9(5) . . ? C45 C46 C47 121.4(5) . . ? F11 C47 F12 106.0(6) . . ? F11 C47 F10 106.0(5) . . ? F12 C47 F10 103.7(5) . . ? F11 C47 C46 112.6(5) . . ? F12 C47 C46 114.1(5) . . ? F10 C47 C46 113.5(6) . . ? C46 C48 C41 120.5(5) . . ? C50 C49 C56 119.5(4) . . ? C50 C49 N3 123.5(4) . . ? C56 C49 N3 117.0(4) . . ? C49 C50 C51 118.8(4) . . ? C53 C51 C50 121.4(5) . . ? C53 C51 C52 121.2(5) . . ? C50 C51 C52 117.4(5) . . ? F14 C52 F13 106.6(6) . . ? F14 C52 F15 105.7(5) . . ? F13 C52 F15 101.7(5) . . ? F14 C52 C51 115.3(5) . . ? F13 C52 C51 113.4(5) . . ? F15 C52 C51 112.9(5) . . ? C54 C53 C51 119.1(5) . . ? C53 C54 C56 121.4(5) . . ? C53 C54 C55 120.8(5) . . ? C56 C54 C55 117.8(5) . . ? F17 C55 F16 108.3(5) . . ? F17 C55 F18 106.7(5) . . ? F16 C55 F18 102.5(5) . . ? F17 C55 C54 113.5(5) . . ? F16 C55 C54 112.8(5) . . ? F18 C55 C54 112.2(5) . . ? C54 C56 C49 119.6(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W O1 0.860(18) 2.02(2) 2.860(6) 166(4) . O1W H2W Cl2 0.865(18) 2.27(3) 3.081(5) 156(4) . N1 H1 Cl1 0.86 2.29 3.126(4) 164.6 . N2 H2 Cl2 0.86 2.39 3.215(4) 160.8 . N3 H3 Cl1 0.86 2.46 3.177(4) 140.6 . _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.249 _refine_diff_density_min -0.508 _refine_diff_density_rms 0.069 _iucr_refine_instructions_details ; TITL SHELX in P2(1)/c CELL 0.71073 13.7878 18.9639 25.3854 90.000 102.004 90.000 ZERR 4 0.0081 0.0104 0.0135 0.000 0.011 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N O F P CL UNIT 224 344 20 8 72 4 8 MERG 2 DFIX 0.84 H1W O1W H2W O1W DFIX 1.4 H1W H2W EADP C38A C38B EADP C39A C39B EADP F4A F4B F5A F5B F6A F6B EXYZ C38A C38B EXYZ C39A C39B HTAB O1W O1 HTAB O1W Cl2 HTAB N1 Cl1 HTAB N2 Cl2 HTAB N3 Cl1 SIZE 0.2 0.16 0.06 FMAP 2 PLAN 20 ACTA 55.00 BOND WGHT 0.09460 12.22900 L.S. 16 DAMP 500.00 15.00 FVAR 1.49928 0.51516 O1W 4 -0.391242 0.446364 0.075580 11.00000 0.06375 0.08170 = 0.12736 0.01081 0.02811 0.01288 H1W 2 -0.350984 0.430300 0.056766 11.00000 -1.50000 H2W 2 -0.418004 0.411187 0.088920 11.00000 -1.50000 MOLE 1 N4 3 0.324242 0.126392 0.076800 11.00000 0.05368 0.04833 = 0.05110 0.00582 0.01389 0.01365 C1 1 0.310647 0.166986 0.024124 11.00000 0.05508 0.05201 = 0.05845 0.01647 0.01437 0.01372 AFIX 23 H1A 2 0.249406 0.193636 0.019490 11.00000 -1.20000 H1B 2 0.364488 0.200620 0.026948 11.00000 -1.20000 AFIX 0 C2 1 0.307538 0.122926 -0.025441 11.00000 0.08560 0.07106 = 0.05238 0.00994 0.00982 0.01106 AFIX 23 H2A 2 0.253676 0.089143 -0.029440 11.00000 -1.20000 H2B 2 0.369227 0.097175 -0.022461 11.00000 -1.20000 AFIX 0 C3 1 0.291851 0.172603 -0.074785 11.00000 0.11066 0.08534 = 0.05932 0.01192 0.00797 -0.01634 AFIX 23 H3A 2 0.228635 0.196453 -0.078090 11.00000 -1.20000 H3B 2 0.343450 0.208236 -0.068938 11.00000 -1.20000 AFIX 0 C4 1 0.293444 0.135691 -0.124655 11.00000 0.18181 0.09665 = 0.07191 -0.00503 0.02492 -0.02743 AFIX 137 H4A 2 0.358928 0.117819 -0.123707 11.00000 -1.50000 H4B 2 0.275217 0.167624 -0.154414 11.00000 -1.50000 H4C 2 0.247241 0.097206 -0.128843 11.00000 -1.50000 AFIX 0 C5 1 0.416007 0.079846 0.084950 11.00000 0.05653 0.05795 = 0.05624 0.00798 0.01643 0.01981 AFIX 23 H5A 2 0.421092 0.054762 0.118715 11.00000 -1.20000 H5B 2 0.405999 0.044881 0.056442 11.00000 -1.20000 AFIX 0 C6 1 0.513199 0.115829 0.085818 11.00000 0.05945 0.06380 = 0.09196 0.00665 0.01921 0.02731 AFIX 23 H6A 2 0.530540 0.145464 0.117528 11.00000 -1.20000 H6B 2 0.508161 0.145416 0.054195 11.00000 -1.20000 AFIX 0 C7 1 0.593404 0.059327 0.086572 11.00000 0.06191 0.07903 = 0.08221 0.01581 0.01671 0.00969 AFIX 23 H7A 2 0.594100 0.028384 0.117074 11.00000 -1.20000 H7B 2 0.575535 0.031081 0.054144 11.00000 -1.20000 AFIX 0 C8 1 0.692496 0.086953 0.089913 11.00000 0.05990 0.07713 = 0.11744 0.00621 0.01380 -0.00016 AFIX 137 H8A 2 0.691236 0.122033 0.062514 11.00000 -1.50000 H8B 2 0.736134 0.049318 0.084732 11.00000 -1.50000 H8C 2 0.715760 0.107809 0.124707 11.00000 -1.50000 AFIX 0 C9 1 0.238643 0.077129 0.079007 11.00000 0.06086 0.03801 = 0.05031 -0.00274 0.01079 0.00448 AFIX 23 H9A 2 0.239361 0.039662 0.053078 11.00000 -1.20000 H9B 2 0.250775 0.055576 0.114426 11.00000 -1.20000 AFIX 0 C10 1 0.135729 0.108623 0.068245 11.00000 0.05799 0.03556 = 0.05039 0.00286 0.01511 0.00124 AFIX 23 H10A 2 0.118297 0.125790 0.031493 11.00000 -1.20000 H10B 2 0.133476 0.147970 0.092376 11.00000 -1.20000 AFIX 0 C11 1 0.062446 0.051387 0.077247 11.00000 0.06661 0.03728 = 0.06156 -0.00099 0.01434 -0.00247 AFIX 23 H11A 2 0.068386 0.011507 0.054199 11.00000 -1.20000 H11B 2 0.080593 0.035358 0.114279 11.00000 -1.20000 AFIX 0 C12 1 -0.044433 0.075261 0.066032 11.00000 0.07754 0.04772 = 0.06616 0.00723 0.02025 0.00067 AFIX 137 H12A 2 -0.050552 0.116310 0.087232 11.00000 -1.50000 H12B 2 -0.085297 0.038167 0.075234 11.00000 -1.50000 H12C 2 -0.065354 0.086475 0.028506 11.00000 -1.50000 AFIX 0 C13 1 0.332946 0.184567 0.119455 11.00000 0.04168 0.04738 = 0.06579 -0.00710 0.00928 0.00512 AFIX 23 H13A 2 0.389010 0.214179 0.116647 11.00000 -1.20000 H13B 2 0.273930 0.213685 0.110816 11.00000 -1.20000 AFIX 0 C14 1 0.345538 0.160936 0.177022 11.00000 0.06231 0.07316 = 0.05810 -0.00716 0.00706 0.01669 AFIX 23 H14A 2 0.402382 0.129843 0.186369 11.00000 -1.20000 H14B 2 0.287104 0.135419 0.181954 11.00000 -1.20000 AFIX 0 C15 1 0.360910 0.226604 0.213125 11.00000 0.07122 0.07756 = 0.06069 -0.01733 0.00592 0.01349 AFIX 23 H15A 2 0.418540 0.251997 0.206874 11.00000 -1.20000 H15B 2 0.303863 0.257305 0.202737 11.00000 -1.20000 AFIX 0 C16 1 0.374980 0.210958 0.271621 11.00000 0.10579 0.10599 = 0.08754 -0.00892 0.01010 0.01991 AFIX 137 H16A 2 0.317637 0.186787 0.278412 11.00000 -1.50000 H16B 2 0.383912 0.254266 0.291627 11.00000 -1.50000 H16C 2 0.432474 0.181718 0.282592 11.00000 -1.50000 AFIX 0 MOLE 2 N5 3 -0.312115 0.512432 -0.090449 11.00000 0.03718 0.07414 = 0.04772 0.00908 0.00907 -0.01027 C17 1 -0.400132 0.470758 -0.079388 11.00000 0.04231 0.09573 = 0.06257 0.00373 0.00908 -0.01503 AFIX 23 H17A 2 -0.386343 0.458113 -0.041537 11.00000 -1.20000 H17B 2 -0.457557 0.501555 -0.085708 11.00000 -1.20000 AFIX 0 C18 1 -0.427372 0.403862 -0.112202 11.00000 0.04545 0.09696 = 0.10762 -0.01381 0.02045 -0.01787 AFIX 23 H18A 2 -0.371807 0.371390 -0.105425 11.00000 -1.20000 H18B 2 -0.442050 0.415267 -0.150284 11.00000 -1.20000 AFIX 0 C19 1 -0.519049 0.368574 -0.096736 11.00000 0.05878 0.16391 = 0.11930 0.03044 0.00125 -0.00906 AFIX 23 H19A 2 -0.570934 0.403686 -0.099095 11.00000 -1.20000 H19B 2 -0.543410 0.332135 -0.122973 11.00000 -1.20000 AFIX 0 C20 1 -0.502256 0.339272 -0.046651 11.00000 0.07686 0.16575 = 0.20380 0.08791 0.02062 -0.01850 AFIX 137 H20A 2 -0.444876 0.309404 -0.041908 11.00000 -1.50000 H20B 2 -0.558841 0.311822 -0.042752 11.00000 -1.50000 H20C 2 -0.491218 0.375946 -0.020004 11.00000 -1.50000 AFIX 0 C21 1 -0.297688 0.577267 -0.055123 11.00000 0.02893 0.06108 = 0.05869 0.01550 0.01054 0.00481 AFIX 23 H21A 2 -0.358743 0.604291 -0.062632 11.00000 -1.20000 H21B 2 -0.246630 0.606116 -0.065475 11.00000 -1.20000 AFIX 0 C22 1 -0.269013 0.564680 0.005798 11.00000 0.05905 0.06308 = 0.05786 0.00834 0.02578 0.00507 AFIX 23 H22A 2 -0.325150 0.544873 0.018210 11.00000 -1.20000 H22B 2 -0.215062 0.530922 0.013501 11.00000 -1.20000 AFIX 0 C23 1 -0.237755 0.631922 0.035444 11.00000 0.06771 0.06109 = 0.06272 0.00292 0.01332 0.00567 AFIX 23 H23A 2 -0.290656 0.666298 0.026193 11.00000 -1.20000 H23B 2 -0.179949 0.650518 0.023974 11.00000 -1.20000 AFIX 0 C24 1 -0.212952 0.621698 0.096992 11.00000 0.08671 0.08478 = 0.06089 -0.00469 0.02485 0.00884 AFIX 137 H24A 2 -0.271572 0.607443 0.108993 11.00000 -1.50000 H24B 2 -0.188897 0.665276 0.114097 11.00000 -1.50000 H24C 2 -0.162930 0.586005 0.106237 11.00000 -1.50000 AFIX 0 C25 1 -0.223462 0.464915 -0.078116 11.00000 0.04065 0.06680 = 0.03870 0.00063 0.00617 -0.01536 AFIX 23 H25A 2 -0.233123 0.427021 -0.104355 11.00000 -1.20000 H25B 2 -0.220872 0.443818 -0.043042 11.00000 -1.20000 AFIX 0 C26 1 -0.123225 0.499207 -0.077941 11.00000 0.03843 0.05579 = 0.04109 -0.00464 0.01066 -0.00391 AFIX 23 H26A 2 -0.112596 0.537889 -0.052385 11.00000 -1.20000 H26B 2 -0.122835 0.518167 -0.113385 11.00000 -1.20000 AFIX 0 C27 1 -0.039698 0.445248 -0.062615 11.00000 0.03993 0.07744 = 0.06218 -0.01779 0.00671 -0.00312 AFIX 23 H27A 2 0.022993 0.469309 -0.060800 11.00000 -1.20000 H27B 2 -0.040396 0.427737 -0.026793 11.00000 -1.20000 AFIX 0 C28 1 -0.043614 0.383050 -0.099811 11.00000 0.08179 0.06904 = 0.09889 -0.01964 0.00611 -0.00327 AFIX 137 H28A 2 -0.103755 0.357159 -0.100675 11.00000 -1.50000 H28B 2 0.012332 0.352951 -0.087078 11.00000 -1.50000 H28C 2 -0.041916 0.399363 -0.135407 11.00000 -1.50000 AFIX 0 C29 1 -0.327729 0.535002 -0.149987 11.00000 0.04352 0.09923 = 0.05470 0.02159 0.00960 -0.00837 AFIX 23 H29A 2 -0.274973 0.567326 -0.153589 11.00000 -1.20000 H29B 2 -0.321036 0.493573 -0.171358 11.00000 -1.20000 AFIX 0 C30 1 -0.422365 0.568583 -0.172760 11.00000 0.05653 0.09643 = 0.07321 0.00103 -0.00084 -0.00349 AFIX 23 H30A 2 -0.428396 0.612271 -0.153828 11.00000 -1.20000 H30B 2 -0.476434 0.537794 -0.168576 11.00000 -1.20000 AFIX 0 C31 1 -0.428389 0.584033 -0.233571 11.00000 0.07349 0.07901 = 0.05297 0.00362 -0.00084 -0.00849 AFIX 23 H31A 2 -0.481822 0.617374 -0.245432 11.00000 -1.20000 H31B 2 -0.367235 0.606948 -0.237222 11.00000 -1.20000 AFIX 0 C32 1 -0.444754 0.521950 -0.270909 11.00000 0.07528 0.07013 = 0.06696 0.00386 -0.00987 0.01504 AFIX 137 H32A 2 -0.387830 0.491601 -0.263230 11.00000 -1.50000 H32B 2 -0.454644 0.538102 -0.307479 11.00000 -1.50000 H32C 2 -0.502270 0.496383 -0.265932 11.00000 -1.50000 AFIX 0 MOLE 3 P1 6 -0.182033 0.331848 0.062466 11.00000 0.03221 0.04144 = 0.03509 0.00527 0.00550 0.00633 O1 4 -0.256696 0.371465 0.024023 11.00000 0.04642 0.05934 = 0.04374 0.01529 0.00747 0.01821 N1 3 -0.115271 0.278350 0.033620 11.00000 0.03091 0.04913 = 0.03094 -0.00734 0.00042 0.00547 AFIX 43 H1 2 -0.053369 0.275776 0.048519 11.00000 -1.20000 AFIX 0 N2 3 -0.239024 0.289540 0.103630 11.00000 0.03053 0.04631 = 0.03777 0.00393 0.00462 -0.00309 AFIX 43 H2 2 -0.302332 0.286197 0.093273 11.00000 -1.20000 AFIX 0 N3 3 -0.089936 0.375930 0.100030 11.00000 0.03256 0.03290 = 0.03572 -0.00152 0.01116 -0.00074 AFIX 43 H3 2 -0.035250 0.376478 0.088787 11.00000 -1.20000 AFIX 0 C33 1 -0.146086 0.236592 -0.011911 11.00000 0.04436 0.03727 = 0.03137 0.00676 0.00178 0.00008 C34 1 -0.077284 0.214921 -0.041252 11.00000 0.06261 0.04005 = 0.03447 -0.00168 0.00888 -0.00731 AFIX 43 H34 2 -0.011469 0.228809 -0.030357 11.00000 -1.20000 AFIX 0 C35 1 -0.104461 0.173387 -0.086047 11.00000 0.08560 0.04110 = 0.03903 -0.00389 0.00564 -0.00441 C36 1 -0.026794 0.151991 -0.116690 11.00000 0.10424 0.06432 = 0.04391 -0.01384 0.01584 -0.00566 C37 1 -0.199914 0.150268 -0.102360 11.00000 0.10973 0.03281 = 0.04188 -0.00133 -0.00226 0.00556 AFIX 43 H37 2 -0.217350 0.120969 -0.132209 11.00000 -1.20000 AFIX 0 PART 1 C38A 1 -0.271459 0.171524 -0.073243 21.00000 0.06692 0.04028 = 0.05872 0.00823 -0.01687 -0.00887 C39A 1 -0.377105 0.147443 -0.088126 21.00000 0.12133 0.06023 = 0.07852 -0.00105 -0.04511 -0.00916 F4A 5 -0.379605 0.097164 -0.132806 21.00000 0.08333 0.10886 = 0.08690 -0.00477 -0.01401 -0.03178 F5A 5 -0.429256 0.199529 -0.113433 21.00000 0.08333 0.10886 = 0.08690 -0.00477 -0.01401 -0.03178 F6A 5 -0.403422 0.109664 -0.054801 21.00000 0.08333 0.10886 = 0.08690 -0.00477 -0.01401 -0.03178 PART 2 C38B 1 -0.271459 0.171524 -0.073243 -21.00000 0.06692 0.04028 = 0.05872 0.00823 -0.01687 -0.00887 C39B 1 -0.377105 0.147443 -0.088126 -21.00000 0.12133 0.06023 = 0.07852 -0.00105 -0.04511 -0.00916 F4B 5 -0.432125 0.159605 -0.048799 -21.00000 0.08333 0.10886 = 0.08690 -0.00477 -0.01401 -0.03178 F5B 5 -0.387104 0.077747 -0.094464 -21.00000 0.08333 0.10886 = 0.08690 -0.00477 -0.01401 -0.03178 F6B 5 -0.433502 0.174227 -0.131602 -21.00000 0.08333 0.10886 = 0.08690 -0.00477 -0.01401 -0.03178 PART 0 C40 1 -0.244776 0.214835 -0.028126 11.00000 0.05593 0.03705 = 0.04593 0.00492 -0.00159 -0.00053 AFIX 43 H40 2 -0.292074 0.229096 -0.009030 11.00000 -1.20000 AFIX 0 C41 1 -0.198843 0.258226 0.153162 11.00000 0.04958 0.02632 = 0.03496 -0.00205 0.00910 -0.00794 C42 1 -0.098672 0.239991 0.167667 11.00000 0.04897 0.03362 = 0.03736 -0.00165 0.01337 -0.00067 AFIX 43 H42 2 -0.056690 0.246156 0.143713 11.00000 -1.20000 AFIX 0 SAME 0.01 C38B > F6B C43 1 -0.063176 0.212326 0.218924 11.00000 0.06241 0.02701 = 0.03479 0.00030 0.00426 0.00028 C44 1 0.045628 0.197573 0.234985 11.00000 0.06841 0.06853 = 0.04820 0.00944 0.00197 0.01637 F7 5 0.077947 0.158089 0.197136 11.00000 0.06333 0.08570 = 0.06149 0.00298 0.00222 0.03052 F8 5 0.069585 0.159957 0.280291 11.00000 0.10162 0.10638 = 0.05512 0.03416 0.00120 0.03939 F9 5 0.101777 0.254563 0.241112 11.00000 0.05683 0.07274 = 0.11631 0.00435 -0.01931 0.00041 C45 1 -0.124646 0.201155 0.254812 11.00000 0.09026 0.04308 = 0.03348 0.01566 0.01220 -0.00381 AFIX 43 H45 2 -0.099540 0.182595 0.288825 11.00000 -1.20000 AFIX 0 C46 1 -0.224115 0.218072 0.239230 11.00000 0.07308 0.04519 = 0.04144 0.00679 0.01777 -0.00575 C47 1 -0.294460 0.205795 0.275591 11.00000 0.10497 0.07817 = 0.05396 0.02290 0.04274 0.00003 C48 1 -0.260902 0.246957 0.189566 11.00000 0.05688 0.03813 = 0.05654 -0.00903 0.02479 -0.00966 AFIX 43 H48 2 -0.327583 0.259154 0.179991 11.00000 -1.20000 AFIX 0 C49 1 -0.089563 0.412805 0.148221 11.00000 0.04906 0.02614 = 0.04130 0.00652 0.01530 0.00620 C50 1 -0.175339 0.434729 0.164171 11.00000 0.05186 0.03980 = 0.04215 0.00700 0.01059 0.00750 AFIX 43 H50 2 -0.237326 0.426851 0.142235 11.00000 -1.20000 AFIX 0 C51 1 -0.166714 0.468867 0.213833 11.00000 0.06536 0.03438 = 0.04370 0.00845 0.02155 0.01607 C52 1 -0.259408 0.486794 0.231258 11.00000 0.07940 0.07612 = 0.04912 0.00216 0.02275 0.02493 C53 1 -0.075315 0.483737 0.245810 11.00000 0.07883 0.03489 = 0.03947 0.00432 0.01159 0.00787 AFIX 43 H53 2 -0.070704 0.507892 0.278120 11.00000 -1.20000 AFIX 0 C54 1 0.008446 0.462517 0.229411 11.00000 0.06142 0.03506 = 0.04204 0.00479 0.00977 0.00178 C55 1 0.109454 0.480171 0.261984 11.00000 0.07541 0.06347 = 0.05866 -0.01083 0.00098 0.00495 C56 1 0.003300 0.425628 0.181946 11.00000 0.04780 0.03294 = 0.04391 0.00539 0.01444 0.00058 AFIX 43 H56 2 0.060917 0.409396 0.172388 11.00000 -1.20000 AFIX 0 F1 5 0.021027 0.207848 -0.130614 11.00000 0.13725 0.05796 = 0.07526 0.00382 0.06131 0.00657 F2 5 0.045166 0.111362 -0.086239 11.00000 0.12091 0.06922 = 0.09657 0.01370 0.05298 0.02876 F3 5 -0.061426 0.116480 -0.160531 11.00000 0.16693 0.14643 = 0.09647 -0.08041 0.04677 -0.02257 F10 5 -0.250813 0.190810 0.324865 11.00000 0.13924 0.21863 = 0.07849 0.06103 0.05854 0.02553 F11 5 -0.355325 0.154133 0.259530 11.00000 0.25111 0.13490 = 0.16310 -0.06926 0.16177 -0.12408 F12 5 -0.349406 0.259955 0.280879 11.00000 0.15016 0.10464 = 0.11532 0.01873 0.09763 0.01604 F13 5 -0.320945 0.433592 0.228404 11.00000 0.08416 0.14293 = 0.17924 -0.06210 0.08109 -0.01208 F14 5 -0.308584 0.537766 0.205994 11.00000 0.15975 0.20242 = 0.13353 0.09001 0.08990 0.14249 F15 5 -0.244626 0.503840 0.283615 11.00000 0.09949 0.16792 = 0.07275 -0.03474 0.03445 0.03262 F16 5 0.172854 0.426673 0.265368 11.00000 0.09051 0.09865 = 0.11480 -0.03027 -0.03482 0.01556 F17 5 0.108374 0.501737 0.310697 11.00000 0.09266 0.16018 = 0.05665 -0.04214 0.00297 -0.02353 F18 5 0.154357 0.530811 0.238867 11.00000 0.08337 0.10650 = 0.09883 0.00322 0.00739 -0.03818 MOLE 4 CL1 7 0.108852 0.300968 0.085442 11.00000 0.03398 0.04238 = 0.07186 -0.00743 0.01335 -0.00048 MOLE 5 CL2 7 -0.475482 0.299181 0.091351 11.00000 0.04369 0.07331 = 0.13937 0.02701 0.03612 0.00628 HKLF 4 END ;