# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Neil Burford' _publ_contact_author_address ; Department of Chemistry Dalhousie University Halifax Nova Scotia B3H 4J3 CANADA ; _publ_contact_author_email NEIL.BURFORD@DAL.CA _publ_section_title ; Bifunctional Diphosphorus Lewis Acids from cyclo-Diphosphadiazanes ; _publ_section_references ; Bruker (2006). SAINT. Version 7.23A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (1999). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (2000). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G.M. (1997). SHELXL97 & SHELXS97. University of Gottingen, Germany. Sheldrick, G.M. (1997b). SADABS. Version 2.10. Bruker AXS Inc., Madison, Wisconsin, USA. ; loop_ _publ_author_name 'Andreas Decken' 'Neil Burford' 'T. Cameron' 'Reagan J. Davidson' 'Jan Weigand' ; U.Werner-Zwanziger ; # Attachment 'NB070164_650720.cif' data_nb070164 _database_code_depnum_ccdc_archive 'CCDC 650720' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H44 Cl6 F6 N6 O6 P2 S2' _chemical_formula_weight 1097.52 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' S S 0.1246 0.1234 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.872(4) _cell_length_b 12.643(5) _cell_length_c 18.914(8) _cell_angle_alpha 99.381(5) _cell_angle_beta 101.844(6) _cell_angle_gamma 97.875(6) _cell_volume 2471.1(17) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 6570 _cell_measurement_theta_min 2.2445 _cell_measurement_theta_max 28.003 _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.275 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.475 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1124 _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8050 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997b)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 16613 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.49 _reflns_number_total 10597 _reflns_number_gt 6494 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0952P)^2^+3.8520P] 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 10597 _refine_ls_number_parameters 576 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1179 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.2139 _refine_ls_wR_factor_gt 0.1744 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.73078(10) 1.12447(8) 0.38289(6) 0.0268(2) Uani 1 1 d . . . P2 P 0.55514(10) 0.96501(8) 0.37864(6) 0.0254(2) Uani 1 1 d . . . N1 N 0.5701(3) 1.0798(2) 0.34137(17) 0.0258(7) Uani 1 1 d . . . N2 N 0.7205(3) 0.9900(2) 0.39233(18) 0.0263(7) Uani 1 1 d . . . C1 C 0.4732(4) 1.1475(3) 0.3269(2) 0.0286(8) Uani 1 1 d . . . C2 C 0.4273(4) 1.1567(3) 0.2536(2) 0.0370(10) Uani 1 1 d . . . C3 C 0.3316(5) 1.2199(4) 0.2392(3) 0.0469(12) Uani 1 1 d . . . H3 H 0.2980 1.2264 0.1899 0.056 Uiso 1 1 calc R . . C4 C 0.2856(5) 1.2728(4) 0.2953(3) 0.0496(12) Uani 1 1 d . . . H4 H 0.2207 1.3149 0.2846 0.060 Uiso 1 1 calc R . . C5 C 0.3341(5) 1.2645(4) 0.3671(3) 0.0433(11) Uani 1 1 d . . . H5 H 0.3027 1.3021 0.4055 0.052 Uiso 1 1 calc R . . C6 C 0.4283(4) 1.2018(3) 0.3847(2) 0.0341(9) Uani 1 1 d . . . C7 C 0.4766(6) 1.1022(4) 0.1907(3) 0.0524(13) Uani 1 1 d . . . H7A H 0.5688 1.1053 0.2068 0.079 Uiso 1 1 calc R . . H7B H 0.4592 1.1400 0.1493 0.079 Uiso 1 1 calc R . . H7C H 0.4337 1.0260 0.1750 0.079 Uiso 1 1 calc R . . C8 C 0.4799(5) 1.1964(4) 0.4645(2) 0.0427(11) Uani 1 1 d . . . H8A H 0.4628 1.1208 0.4708 0.064 Uiso 1 1 calc R . . H8B H 0.4381 1.2417 0.4960 0.064 Uiso 1 1 calc R . . H8C H 0.5722 1.2232 0.4783 0.064 Uiso 1 1 calc R . . C9 C 0.7996(4) 0.9403(3) 0.4454(2) 0.0290(8) Uani 1 1 d . . . C10 C 0.8207(4) 0.9806(3) 0.5219(2) 0.0325(9) Uani 1 1 d . . . C11 C 0.8841(4) 0.9224(4) 0.5699(3) 0.0418(11) Uani 1 1 d . . . H11 H 0.8986 0.9480 0.6215 0.050 Uiso 1 1 calc R . . C12 C 0.9263(4) 0.8284(4) 0.5441(3) 0.0456(12) Uani 1 1 d . . . H12 H 0.9681 0.7894 0.5779 0.055 Uiso 1 1 calc R . . C13 C 0.9075(4) 0.7916(4) 0.4695(3) 0.0452(12) Uani 1 1 d . . . H13 H 0.9376 0.7273 0.4523 0.054 Uiso 1 1 calc R . . C14 C 0.8454(4) 0.8461(3) 0.4183(3) 0.0389(10) Uani 1 1 d . . . C15 C 0.7725(5) 1.0807(4) 0.5526(2) 0.0405(10) Uani 1 1 d . . . H15A H 0.7912 1.0914 0.6065 0.061 Uiso 1 1 calc R . . H15B H 0.6801 1.0712 0.5331 0.061 Uiso 1 1 calc R . . H15C H 0.8150 1.1445 0.5381 0.061 Uiso 1 1 calc R . . C16 C 0.8322(6) 0.8026(4) 0.3373(3) 0.0614(15) Uani 1 1 d . . . H16A H 0.8964 0.8464 0.3194 0.092 Uiso 1 1 calc R . . H16B H 0.7467 0.8065 0.3097 0.092 Uiso 1 1 calc R . . H16C H 0.8448 0.7266 0.3301 0.092 Uiso 1 1 calc R . . N17 N 0.8063(3) 1.1316(2) 0.30769(18) 0.0273(7) Uani 1 1 d . . . C18 C 0.8493(4) 1.2344(3) 0.2980(2) 0.0325(9) Uani 1 1 d . . . H18 H 0.8393 1.2951 0.3319 0.039 Uiso 1 1 calc R . . C19 C 0.9048(4) 1.2534(3) 0.2428(2) 0.0355(10) Uani 1 1 d . . . H19 H 0.9315 1.3263 0.2383 0.043 Uiso 1 1 calc R . . C20 C 0.9239(4) 1.1652(3) 0.1909(2) 0.0305(9) Uani 1 1 d . . . C21 C 0.8836(4) 1.0594(3) 0.2032(2) 0.0356(10) Uani 1 1 d . . . H21 H 0.8972 0.9973 0.1720 0.043 Uiso 1 1 calc R . . C22 C 0.8261(4) 1.0461(3) 0.2589(2) 0.0349(10) Uani 1 1 d . . . H22 H 0.7979 0.9741 0.2645 0.042 Uiso 1 1 calc R . . N23 N 0.9782(4) 1.1806(3) 0.1356(2) 0.0377(9) Uani 1 1 d . . . C24 C 1.0138(6) 1.2894(4) 0.1211(3) 0.0528(14) Uani 1 1 d . . . H24A H 0.9374 1.3136 0.0963 0.079 Uiso 1 1 calc R . . H24B H 1.0748 1.2872 0.0895 0.079 Uiso 1 1 calc R . . H24C H 1.0531 1.3403 0.1678 0.079 Uiso 1 1 calc R . . C25 C 1.0009(6) 1.0900(4) 0.0830(3) 0.0538(14) Uani 1 1 d . . . H25A H 1.0531 1.0455 0.1098 0.081 Uiso 1 1 calc R . . H25B H 1.0458 1.1194 0.0485 0.081 Uiso 1 1 calc R . . H25C H 0.9190 1.0451 0.0556 0.081 Uiso 1 1 calc R . . N26 N 0.4992(3) 0.8546(2) 0.30231(18) 0.0273(7) Uani 1 1 d . . . C27 C 0.5338(4) 0.8433(3) 0.2360(2) 0.0325(9) Uani 1 1 d . . . H27 H 0.5886 0.9023 0.2269 0.039 Uiso 1 1 calc R . . C28 C 0.4936(4) 0.7526(3) 0.1832(2) 0.0364(10) Uani 1 1 d . . . H28 H 0.5202 0.7488 0.1382 0.044 Uiso 1 1 calc R . . C29 C 0.4112(4) 0.6621(3) 0.1947(2) 0.0359(10) Uani 1 1 d . . . C30 C 0.3726(5) 0.6762(3) 0.2623(3) 0.0429(11) Uani 1 1 d . . . H30 H 0.3147 0.6198 0.2718 0.052 Uiso 1 1 calc R . . C31 C 0.4170(4) 0.7687(3) 0.3131(2) 0.0365(10) Uani 1 1 d . . . H31 H 0.3906 0.7751 0.3583 0.044 Uiso 1 1 calc R . . N32 N 0.3726(4) 0.5704(3) 0.1446(2) 0.0464(10) Uani 1 1 d . . . C33 C 0.4041(6) 0.5568(5) 0.0725(3) 0.0689(18) Uani 1 1 d . . . H33A H 0.3509 0.5949 0.0405 0.103 Uiso 1 1 calc R . . H33B H 0.3882 0.4791 0.0502 0.103 Uiso 1 1 calc R . . H33C H 0.4943 0.5872 0.0784 0.103 Uiso 1 1 calc R . . C34 C 0.2845(7) 0.4799(4) 0.1567(4) 0.078(2) Uani 1 1 d . . . H34A H 0.3253 0.4531 0.1998 0.118 Uiso 1 1 calc R . . H34B H 0.2629 0.4209 0.1132 0.118 Uiso 1 1 calc R . . H34C H 0.2065 0.5053 0.1651 0.118 Uiso 1 1 calc R . . C35 C 0.1528(6) 0.5419(5) 0.4208(4) 0.0686(17) Uani 1 1 d . . . C36 C 0.6227(5) 0.8900(4) 0.0265(3) 0.0453(11) Uani 1 1 d . . . C37 C 0.1042(7) 0.8000(6) 0.1739(4) 0.085(2) Uani 1 1 d . . . H37A H 0.0118 0.8009 0.1578 0.102 Uiso 1 1 calc R . . H37B H 0.1143 0.7423 0.2032 0.102 Uiso 1 1 calc R . . C38 C 0.7780(9) 0.5158(8) 0.1455(5) 0.121(3) Uani 1 1 d . . . H38A H 0.8187 0.5197 0.1979 0.146 Uiso 1 1 calc R . . H38B H 0.7238 0.5726 0.1430 0.146 Uiso 1 1 calc R . . C39 C 0.6533(11) 0.4818(13) 0.3701(6) 0.173(5) Uani 1 1 d . . . H39A H 0.7431 0.5192 0.3805 0.208 Uiso 1 1 calc R . . H39B H 0.6547 0.4142 0.3902 0.208 Uiso 1 1 calc R . . F1 F 0.2792(4) 0.5689(5) 0.4287(3) 0.1267(18) Uani 1 1 d . . . F2 F 0.1286(4) 0.4387(3) 0.4283(2) 0.0927(13) Uani 1 1 d . . . F3 F 0.1203(5) 0.6025(3) 0.4777(2) 0.0971(14) Uani 1 1 d . . . F4 F 0.6694(4) 0.9735(3) 0.0004(2) 0.0752(10) Uani 1 1 d . . . F5 F 0.5065(3) 0.8516(3) -0.0148(2) 0.0771(10) Uani 1 1 d . . . F6 F 0.6120(3) 0.9295(2) 0.09486(17) 0.0646(9) Uani 1 1 d . . . S1 S 0.06868(13) 0.56241(9) 0.33293(7) 0.0469(3) Uani 1 1 d . . . S2 S 0.72465(11) 0.78643(8) 0.02710(6) 0.0374(3) Uani 1 1 d . . . O1 O 0.1062(5) 0.6758(3) 0.3357(2) 0.0742(13) Uani 1 1 d . . . O2 O 0.1158(4) 0.4913(3) 0.2814(2) 0.0597(10) Uani 1 1 d . . . O3 O -0.0631(4) 0.5297(4) 0.3332(3) 0.0740(12) Uani 1 1 d . . . O4 O 0.8448(4) 0.8427(3) 0.0734(2) 0.0648(11) Uani 1 1 d . . . O5 O 0.7270(4) 0.7570(3) -0.0489(2) 0.0618(10) Uani 1 1 d . . . O6 O 0.6568(4) 0.7038(3) 0.0548(2) 0.0644(11) Uani 1 1 d . . . Cl1 Cl 0.1681(3) 0.7706(3) 0.09603(13) 0.1484(12) Uani 1 1 d . . . Cl2 Cl 0.18104(18) 0.92569(15) 0.22841(10) 0.0840(5) Uani 1 1 d . . . Cl3 Cl 0.9076(3) 0.54362(19) 0.0926(2) 0.1706(16) Uani 1 1 d . . . Cl4 Cl 0.6890(3) 0.3961(3) 0.11151(17) 0.1592(13) Uani 1 1 d . . . Cl5 Cl 0.6065(3) 0.4448(4) 0.2824(2) 0.1976(19) Uani 1 1 d . . . Cl6 Cl 0.5805(4) 0.5591(3) 0.4191(2) 0.1904(17) 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 P1 0.0296(5) 0.0223(5) 0.0275(5) 0.0001(4) 0.0098(4) 0.0025(4) P2 0.0280(5) 0.0227(5) 0.0255(5) 0.0022(4) 0.0094(4) 0.0036(4) N1 0.0286(17) 0.0229(15) 0.0274(17) 0.0045(13) 0.0095(14) 0.0055(13) N2 0.0264(17) 0.0233(15) 0.0276(17) 0.0007(13) 0.0079(14) 0.0021(13) C1 0.031(2) 0.0231(18) 0.032(2) 0.0063(16) 0.0079(17) 0.0039(15) C2 0.043(3) 0.035(2) 0.034(2) 0.0065(18) 0.010(2) 0.0101(19) C3 0.050(3) 0.046(3) 0.047(3) 0.016(2) 0.007(2) 0.016(2) C4 0.047(3) 0.041(3) 0.068(4) 0.020(2) 0.013(3) 0.021(2) C5 0.048(3) 0.037(2) 0.054(3) 0.010(2) 0.023(2) 0.018(2) C6 0.037(2) 0.029(2) 0.039(2) 0.0059(18) 0.014(2) 0.0085(17) C7 0.072(4) 0.058(3) 0.032(3) 0.011(2) 0.013(2) 0.026(3) C8 0.060(3) 0.040(2) 0.036(2) 0.0049(19) 0.022(2) 0.021(2) C9 0.026(2) 0.0301(19) 0.031(2) 0.0068(16) 0.0065(17) 0.0023(16) C10 0.027(2) 0.035(2) 0.033(2) 0.0048(17) 0.0060(18) -0.0008(17) C11 0.034(2) 0.052(3) 0.035(2) 0.012(2) -0.001(2) 0.001(2) C12 0.034(2) 0.041(2) 0.059(3) 0.022(2) -0.002(2) 0.002(2) C13 0.037(3) 0.036(2) 0.063(3) 0.012(2) 0.005(2) 0.0108(19) C14 0.039(2) 0.033(2) 0.044(3) 0.0065(19) 0.008(2) 0.0098(18) C15 0.047(3) 0.045(2) 0.028(2) -0.0003(19) 0.010(2) 0.008(2) C16 0.085(4) 0.051(3) 0.051(3) -0.002(2) 0.013(3) 0.039(3) N17 0.0278(17) 0.0251(15) 0.0289(17) 0.0040(13) 0.0095(14) 0.0016(13) C18 0.039(2) 0.0232(18) 0.036(2) 0.0018(16) 0.0125(19) 0.0042(16) C19 0.044(3) 0.0229(19) 0.043(3) 0.0079(17) 0.018(2) 0.0023(17) C20 0.028(2) 0.030(2) 0.032(2) 0.0039(17) 0.0094(18) -0.0002(16) C21 0.040(2) 0.0246(19) 0.040(2) -0.0035(17) 0.018(2) -0.0032(17) C22 0.040(2) 0.0215(18) 0.041(2) -0.0021(17) 0.017(2) -0.0038(17) N23 0.042(2) 0.0337(18) 0.036(2) 0.0018(15) 0.0177(17) -0.0047(15) C24 0.076(4) 0.035(2) 0.054(3) 0.014(2) 0.034(3) 0.000(2) C25 0.070(4) 0.042(3) 0.050(3) -0.004(2) 0.038(3) -0.010(2) N26 0.0296(18) 0.0243(15) 0.0274(17) 0.0027(13) 0.0100(14) 0.0002(13) C27 0.036(2) 0.030(2) 0.030(2) 0.0030(17) 0.0114(18) -0.0022(17) C28 0.041(3) 0.034(2) 0.030(2) -0.0029(17) 0.016(2) -0.0059(18) C29 0.034(2) 0.027(2) 0.042(3) -0.0023(18) 0.011(2) -0.0021(17) C30 0.053(3) 0.030(2) 0.045(3) -0.0020(19) 0.025(2) -0.0080(19) C31 0.042(2) 0.029(2) 0.039(2) 0.0016(18) 0.020(2) -0.0033(18) N32 0.045(2) 0.0348(19) 0.053(2) -0.0112(17) 0.022(2) -0.0086(17) C33 0.080(4) 0.056(3) 0.056(3) -0.027(3) 0.034(3) -0.019(3) C34 0.090(5) 0.038(3) 0.096(5) -0.024(3) 0.052(4) -0.030(3) C35 0.067(4) 0.057(3) 0.080(4) 0.000(3) 0.014(3) 0.023(3) C36 0.056(3) 0.050(3) 0.035(3) 0.009(2) 0.018(2) 0.017(2) C37 0.071(5) 0.088(5) 0.085(5) 0.011(4) -0.008(4) 0.024(4) C38 0.108(7) 0.143(8) 0.100(6) 0.028(6) -0.024(5) 0.043(6) C39 0.131(10) 0.265(16) 0.131(10) 0.002(10) 0.050(8) 0.077(10) F1 0.055(3) 0.155(5) 0.143(4) -0.001(4) -0.010(3) 0.013(3) F2 0.134(4) 0.064(2) 0.097(3) 0.031(2) 0.035(3) 0.047(2) F3 0.142(4) 0.088(3) 0.058(2) -0.009(2) 0.016(2) 0.047(3) F4 0.102(3) 0.0549(19) 0.089(3) 0.0351(18) 0.040(2) 0.0324(18) F5 0.056(2) 0.094(3) 0.076(2) 0.003(2) 0.0055(18) 0.0273(19) F6 0.096(3) 0.0606(19) 0.0484(18) 0.0053(14) 0.0299(17) 0.0376(18) S1 0.0520(7) 0.0324(6) 0.0583(8) 0.0008(5) 0.0239(6) 0.0077(5) S2 0.0418(6) 0.0278(5) 0.0417(6) -0.0012(4) 0.0157(5) 0.0033(4) O1 0.106(3) 0.0313(18) 0.094(3) 0.0079(19) 0.046(3) 0.012(2) O2 0.077(3) 0.0367(18) 0.068(2) -0.0055(16) 0.037(2) 0.0060(17) O3 0.041(2) 0.087(3) 0.092(3) 0.007(2) 0.019(2) 0.009(2) O4 0.052(2) 0.0420(19) 0.082(3) -0.0108(18) -0.010(2) 0.0095(16) O5 0.079(3) 0.062(2) 0.050(2) -0.0022(18) 0.033(2) 0.020(2) O6 0.079(3) 0.0434(19) 0.090(3) 0.0248(19) 0.052(2) 0.0160(18) Cl1 0.123(2) 0.222(3) 0.0882(16) -0.0173(18) -0.0076(14) 0.095(2) Cl2 0.0795(12) 0.0820(11) 0.0835(12) 0.0164(9) 0.0064(10) 0.0088(9) Cl3 0.118(2) 0.0755(14) 0.276(4) 0.0411(19) -0.050(2) 0.0117(14) Cl4 0.173(3) 0.150(2) 0.128(2) 0.050(2) -0.015(2) -0.017(2) Cl5 0.099(2) 0.248(4) 0.184(3) -0.095(3) 0.035(2) -0.021(2) Cl6 0.180(3) 0.217(4) 0.156(3) -0.050(3) 0.017(2) 0.110(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N2 1.730(3) . ? P1 N1 1.735(3) . ? P1 N17 1.790(3) . ? P1 P2 2.5587(15) . ? P2 N1 1.717(3) . ? P2 N2 1.740(3) . ? P2 N26 1.775(3) . ? N1 C1 1.457(5) . ? N2 C9 1.462(5) . ? C1 C2 1.403(6) . ? C1 C6 1.404(6) . ? C2 C3 1.407(7) . ? C2 C7 1.508(6) . ? C3 C4 1.379(7) . ? C3 H3 0.9500 . ? C4 C5 1.379(7) . ? C4 H4 0.9500 . ? C5 C6 1.399(6) . ? C5 H5 0.9500 . ? C6 C8 1.514(6) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.413(6) . ? C9 C14 1.413(6) . ? C10 C11 1.393(6) . ? C10 C15 1.511(6) . ? C11 C12 1.383(7) . ? C11 H11 0.9500 . ? C12 C13 1.376(7) . ? C12 H12 0.9500 . ? C13 C14 1.394(7) . ? C13 H13 0.9500 . ? C14 C16 1.513(7) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N17 C22 1.373(5) . ? N17 C18 1.375(5) . ? C18 C19 1.346(6) . ? C18 H18 0.9500 . ? C19 C20 1.428(6) . ? C19 H19 0.9500 . ? C20 N23 1.329(5) . ? C20 C21 1.421(5) . ? C21 C22 1.351(6) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N23 C24 1.463(5) . ? N23 C25 1.473(6) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? N26 C27 1.373(5) . ? N26 C31 1.379(5) . ? C27 C28 1.348(6) . ? C27 H27 0.9500 . ? C28 C29 1.428(6) . ? C28 H28 0.9500 . ? C29 N32 1.328(5) . ? C29 C30 1.418(6) . ? C30 C31 1.347(6) . ? C30 H30 0.9500 . ? C31 H31 0.9500 . ? N32 C33 1.462(6) . ? N32 C34 1.467(6) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C35 F2 1.332(7) . ? C35 F1 1.341(7) . ? C35 F3 1.353(7) . ? C35 S1 1.802(7) . ? C36 F4 1.320(6) . ? C36 F5 1.321(6) . ? C36 F6 1.343(5) . ? C36 S2 1.828(5) . ? C37 Cl2 1.742(7) . ? C37 Cl1 1.762(8) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 Cl4 1.633(10) . ? C38 Cl3 1.915(11) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? C39 Cl5 1.601(12) . ? C39 Cl6 1.631(11) . ? C39 H39A 0.9900 . ? C39 H39B 0.9900 . ? S1 O1 1.426(4) . ? S1 O2 1.436(3) . ? S1 O3 1.437(4) . ? S2 O6 1.427(3) . ? S2 O5 1.431(4) . ? S2 O4 1.432(4) . ? 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 N2 P1 N1 81.49(15) . . ? N2 P1 N17 104.30(15) . . ? N1 P1 N17 104.54(16) . . ? N2 P1 P2 42.63(11) . . ? N1 P1 P2 41.88(10) . . ? N17 P1 P2 121.50(11) . . ? N1 P2 N2 81.73(15) . . ? N1 P2 N26 105.48(16) . . ? N2 P2 N26 105.78(15) . . ? N1 P2 P1 42.43(11) . . ? N2 P2 P1 42.33(11) . . ? N26 P2 P1 123.23(11) . . ? C1 N1 P2 126.1(2) . . ? C1 N1 P1 126.7(2) . . ? P2 N1 P1 95.69(17) . . ? C9 N2 P1 130.1(3) . . ? C9 N2 P2 120.3(2) . . ? P1 N2 P2 95.04(16) . . ? C2 C1 C6 121.5(4) . . ? C2 C1 N1 117.7(4) . . ? C6 C1 N1 120.8(4) . . ? C1 C2 C3 117.9(4) . . ? C1 C2 C7 122.7(4) . . ? C3 C2 C7 119.4(4) . . ? C4 C3 C2 121.2(5) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.5(4) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 118.0(4) . . ? C5 C6 C8 119.5(4) . . ? C1 C6 C8 122.4(4) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 121.0(4) . . ? C10 C9 N2 120.6(4) . . ? C14 C9 N2 118.2(4) . . ? C11 C10 C9 118.0(4) . . ? C11 C10 C15 119.6(4) . . ? C9 C10 C15 122.4(4) . . ? C12 C11 C10 121.5(4) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C13 C12 C11 119.8(4) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 121.7(4) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? C13 C14 C9 117.9(4) . . ? C13 C14 C16 118.6(4) . . ? C9 C14 C16 123.5(4) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C22 N17 C18 116.5(3) . . ? C22 N17 P1 127.4(3) . . ? C18 N17 P1 116.1(3) . . ? C19 C18 N17 123.3(4) . . ? C19 C18 H18 118.4 . . ? N17 C18 H18 118.4 . . ? C18 C19 C20 120.7(4) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? N23 C20 C21 121.9(4) . . ? N23 C20 C19 122.5(4) . . ? C21 C20 C19 115.5(3) . . ? C22 C21 C20 120.6(4) . . ? C22 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C21 C22 N17 123.3(4) . . ? C21 C22 H22 118.4 . . ? N17 C22 H22 118.4 . . ? C20 N23 C24 121.7(4) . . ? C20 N23 C25 122.8(3) . . ? C24 N23 C25 115.4(4) . . ? N23 C24 H24A 109.5 . . ? N23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N23 C25 H25A 109.5 . . ? N23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C27 N26 C31 117.1(3) . . ? C27 N26 P2 127.3(3) . . ? C31 N26 P2 115.5(3) . . ? C28 C27 N26 123.1(4) . . ? C28 C27 H27 118.4 . . ? N26 C27 H27 118.4 . . ? C27 C28 C29 120.2(4) . . ? C27 C28 H28 119.9 . . ? C29 C28 H28 119.9 . . ? N32 C29 C30 122.1(4) . . ? N32 C29 C28 121.7(4) . . ? C30 C29 C28 116.2(4) . . ? C31 C30 C29 120.7(4) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C30 C31 N26 122.7(4) . . ? C30 C31 H31 118.7 . . ? N26 C31 H31 118.7 . . ? C29 N32 C33 123.0(4) . . ? C29 N32 C34 120.7(4) . . ? C33 N32 C34 116.1(4) . . ? N32 C33 H33A 109.5 . . ? N32 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N32 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N32 C34 H34A 109.5 . . ? N32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? F2 C35 F1 107.5(5) . . ? F2 C35 F3 106.4(6) . . ? F1 C35 F3 108.1(5) . . ? F2 C35 S1 112.3(4) . . ? F1 C35 S1 110.3(5) . . ? F3 C35 S1 112.0(4) . . ? F4 C36 F5 106.8(4) . . ? F4 C36 F6 107.0(4) . . ? F5 C36 F6 107.8(4) . . ? F4 C36 S2 111.7(3) . . ? F5 C36 S2 112.2(3) . . ? F6 C36 S2 111.1(3) . . ? Cl2 C37 Cl1 110.7(4) . . ? Cl2 C37 H37A 109.5 . . ? Cl1 C37 H37A 109.5 . . ? Cl2 C37 H37B 109.5 . . ? Cl1 C37 H37B 109.5 . . ? H37A C37 H37B 108.1 . . ? Cl4 C38 Cl3 111.3(6) . . ? Cl4 C38 H38A 109.4 . . ? Cl3 C38 H38A 109.4 . . ? Cl4 C38 H38B 109.4 . . ? Cl3 C38 H38B 109.4 . . ? H38A C38 H38B 108.0 . . ? Cl5 C39 Cl6 122.7(8) . . ? Cl5 C39 H39A 106.7 . . ? Cl6 C39 H39A 106.7 . . ? Cl5 C39 H39B 106.7 . . ? Cl6 C39 H39B 106.7 . . ? H39A C39 H39B 106.6 . . ? O1 S1 O2 115.1(2) . . ? O1 S1 O3 114.6(3) . . ? O2 S1 O3 114.8(2) . . ? O1 S1 C35 103.8(3) . . ? O2 S1 C35 102.9(3) . . ? O3 S1 C35 103.3(3) . . ? O6 S2 O5 114.6(2) . . ? O6 S2 O4 116.4(3) . . ? O5 S2 O4 113.8(3) . . ? O6 S2 C36 102.9(2) . . ? O5 S2 C36 102.8(2) . . ? O4 S2 C36 104.0(2) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.967 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.085 data_nb070148 _database_code_depnum_ccdc_archive 'CCDC 650721' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H18 F6 N2 O6 P2 S2' _chemical_formula_weight 598.40 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' 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 'P 21/c' _symmetry_int_tables_number 14 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 12.985(4) _cell_length_b 10.925(3) _cell_length_c 18.101(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.012(4) _cell_angle_gamma 90.00 _cell_volume 2564.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 7385 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.09 _exptl_crystal_description Irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 0.413 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8361 _exptl_absorpt_correction_T_max 0.9039 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997b)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 17263 _diffrn_reflns_av_R_equivalents 0.0393 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5721 _reflns_number_gt 4520 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0497P)^2^+2.5154P] 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 5721 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1121 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.82444(4) 0.78979(5) 0.13066(3) 0.03150(15) Uani 1 1 d . . . P2 P 0.82356(4) 0.94978(5) 0.02763(3) 0.02891(14) Uani 1 1 d . . . S1 S 0.66131(6) 0.67004(7) 0.20967(4) 0.0547(2) Uani 1 1 d . . . S2 S 0.66600(6) 1.07210(8) -0.06488(4) 0.0566(2) Uani 1 1 d . . . N1 N 0.81819(14) 0.79526(17) 0.03644(10) 0.0317(4) Uani 1 1 d . . . N2 N 0.81150(13) 0.94388(16) 0.12049(10) 0.0284(4) Uani 1 1 d . . . C1 C 0.84604(19) 0.7054(2) -0.01746(13) 0.0364(5) Uani 1 1 d . . . C2 C 0.9502(2) 0.6773(2) -0.02446(15) 0.0442(6) Uani 1 1 d . . . C3 C 0.9743(3) 0.5951(3) -0.07983(18) 0.0599(8) Uani 1 1 d . . . H3 H 1.0444 0.5748 -0.0863 0.072 Uiso 1 1 calc R . . C4 C 0.8975(3) 0.5427(3) -0.12554(17) 0.0676(10) Uani 1 1 d . . . H4 H 0.9154 0.4874 -0.1633 0.081 Uiso 1 1 calc R . . C5 C 0.7959(3) 0.5700(3) -0.11669(17) 0.0635(9) Uani 1 1 d . . . H5 H 0.7441 0.5320 -0.1478 0.076 Uiso 1 1 calc R . . C6 C 0.7673(2) 0.6528(3) -0.06270(15) 0.0485(6) Uani 1 1 d . . . C7 C 1.0339(2) 0.7340(3) 0.02523(19) 0.0564(8) Uani 1 1 d . . . H7A H 1.1011 0.7015 0.0125 0.085 Uiso 1 1 calc R . . H7B H 1.0219 0.7142 0.0769 0.085 Uiso 1 1 calc R . . H7C H 1.0332 0.8230 0.0187 0.085 Uiso 1 1 calc R . . C8 C 0.6551(2) 0.6835(3) -0.05577(19) 0.0647(9) Uani 1 1 d . . . H8A H 0.6345 0.7468 -0.0919 0.097 Uiso 1 1 calc R . . H8B H 0.6446 0.7136 -0.0057 0.097 Uiso 1 1 calc R . . H8C H 0.6132 0.6099 -0.0652 0.097 Uiso 1 1 calc R . . C9 C 0.82409(16) 1.0453(2) 0.17111(11) 0.0287(4) Uani 1 1 d . . . C10 C 0.73712(18) 1.0905(2) 0.20451(12) 0.0344(5) Uani 1 1 d . . . C11 C 0.7495(2) 1.1932(2) 0.24958(14) 0.0438(6) Uani 1 1 d . . . H11 H 0.6919 1.2249 0.2735 0.053 Uiso 1 1 calc R . . C12 C 0.8439(2) 1.2498(3) 0.26005(15) 0.0501(7) Uani 1 1 d . . . H12 H 0.8505 1.3210 0.2901 0.060 Uiso 1 1 calc R . . C13 C 0.9294(2) 1.2034(2) 0.22698(14) 0.0445(6) Uani 1 1 d . . . H13 H 0.9942 1.2431 0.2347 0.053 Uiso 1 1 calc R . . C14 C 0.92163(17) 1.0992(2) 0.18248(12) 0.0328(5) Uani 1 1 d . . . C15 C 0.63215(19) 1.0319(3) 0.19332(16) 0.0478(6) Uani 1 1 d . . . H15A H 0.6257 0.9655 0.2292 0.072 Uiso 1 1 calc R . . H15B H 0.6240 0.9987 0.1430 0.072 Uiso 1 1 calc R . . H15C H 0.5786 1.0933 0.2005 0.072 Uiso 1 1 calc R . . C16 C 1.01647(18) 1.0479(3) 0.14928(15) 0.0449(6) Uani 1 1 d . . . H16A H 1.0106 1.0579 0.0954 0.067 Uiso 1 1 calc R . . H16B H 1.0229 0.9608 0.1615 0.067 Uiso 1 1 calc R . . H16C H 1.0776 1.0918 0.1693 0.067 Uiso 1 1 calc R . . C17 C 0.6413(3) 0.5246(3) 0.1637(3) 0.0758(10) Uani 1 1 d . . . C18 C 0.6352(3) 1.2068(4) -0.0102(3) 0.0807(12) Uani 1 1 d . . . F1 F 0.5721(3) 0.5334(3) 0.10946(18) 0.1362(13) Uani 1 1 d . . . F2 F 0.6110(2) 0.4430(2) 0.21199(17) 0.1083(9) Uani 1 1 d . . . F3 F 0.7287(3) 0.4884(2) 0.1376(2) 0.1388(13) Uani 1 1 d . . . F4 F 0.6131(3) 1.2992(3) -0.05521(19) 0.1348(12) Uani 1 1 d . . . F5 F 0.7156(2) 1.2364(2) 0.03460(15) 0.0977(8) Uani 1 1 d . . . F6 F 0.5565(2) 1.1860(3) 0.0294(2) 0.1537(15) Uani 1 1 d . . . O1 O 0.69671(13) 0.74701(16) 0.14349(10) 0.0425(4) Uani 1 1 d . . . O2 O 0.7425(2) 0.6553(3) 0.26362(14) 0.1061(12) Uani 1 1 d . . . O3 O 0.5635(2) 0.7093(3) 0.2282(2) 0.1069(12) Uani 1 1 d . . . O4 O 0.69569(12) 0.98269(16) -0.00071(10) 0.0406(4) Uani 1 1 d . . . O5 O 0.5744(3) 1.0316(3) -0.1007(2) 0.1289(15) Uani 1 1 d . . . O6 O 0.75304(19) 1.1045(2) -0.10406(12) 0.0705(7) 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 P1 0.0318(3) 0.0318(3) 0.0308(3) 0.0028(2) 0.0016(2) 0.0011(2) P2 0.0289(3) 0.0321(3) 0.0260(3) 0.0005(2) 0.0035(2) -0.0028(2) S1 0.0614(4) 0.0503(4) 0.0539(4) 0.0093(3) 0.0182(3) -0.0146(3) S2 0.0507(4) 0.0620(5) 0.0546(4) 0.0240(4) -0.0198(3) -0.0073(3) N1 0.0353(9) 0.0306(10) 0.0294(9) -0.0019(7) 0.0035(7) -0.0009(7) N2 0.0301(9) 0.0301(9) 0.0251(9) 0.0003(7) 0.0025(7) -0.0005(7) C1 0.0470(13) 0.0295(11) 0.0334(12) -0.0026(9) 0.0082(10) 0.0001(9) C2 0.0517(14) 0.0316(12) 0.0506(15) 0.0029(11) 0.0166(12) 0.0027(11) C3 0.076(2) 0.0438(16) 0.0633(19) 0.0029(14) 0.0309(16) 0.0157(14) C4 0.115(3) 0.0475(18) 0.0416(16) -0.0112(13) 0.0145(17) 0.0137(18) C5 0.094(3) 0.0528(18) 0.0427(16) -0.0157(13) -0.0044(16) 0.0037(17) C6 0.0654(17) 0.0430(15) 0.0369(13) -0.0065(11) -0.0001(12) -0.0037(12) C7 0.0373(13) 0.0460(16) 0.087(2) -0.0017(15) 0.0115(14) 0.0039(11) C8 0.0543(17) 0.074(2) 0.063(2) -0.0168(17) -0.0160(15) -0.0111(15) C9 0.0325(10) 0.0305(11) 0.0230(10) 0.0004(8) 0.0009(8) 0.0007(8) C10 0.0358(11) 0.0377(12) 0.0300(11) -0.0007(9) 0.0037(9) 0.0019(9) C11 0.0515(14) 0.0427(14) 0.0378(13) -0.0066(11) 0.0091(11) 0.0068(11) C12 0.0670(18) 0.0426(15) 0.0407(14) -0.0129(12) 0.0034(13) -0.0055(13) C13 0.0500(14) 0.0460(15) 0.0369(13) -0.0026(11) -0.0035(11) -0.0138(11) C14 0.0339(11) 0.0382(12) 0.0262(10) 0.0034(9) -0.0005(8) -0.0034(9) C15 0.0320(12) 0.0601(17) 0.0522(16) -0.0111(13) 0.0097(11) 0.0004(11) C16 0.0292(11) 0.0585(16) 0.0471(14) 0.0000(12) 0.0017(10) -0.0038(11) C17 0.080(2) 0.0453(18) 0.103(3) 0.0099(19) 0.012(2) -0.0097(17) C18 0.060(2) 0.070(2) 0.114(3) 0.037(2) 0.027(2) 0.0295(18) F1 0.166(3) 0.117(2) 0.120(2) 0.0119(18) -0.048(2) -0.081(2) F2 0.124(2) 0.0497(12) 0.153(2) 0.0399(14) 0.0235(18) -0.0166(12) F3 0.160(3) 0.0620(15) 0.203(3) -0.0155(18) 0.090(3) 0.0098(17) F4 0.151(3) 0.0877(19) 0.168(3) 0.0681(19) 0.028(2) 0.0579(18) F5 0.126(2) 0.0640(14) 0.1045(19) -0.0165(13) 0.0169(16) 0.0124(14) F6 0.1019(19) 0.154(3) 0.214(3) 0.078(3) 0.100(2) 0.075(2) O1 0.0378(9) 0.0405(10) 0.0499(10) 0.0103(8) 0.0093(7) -0.0043(7) O2 0.106(2) 0.155(3) 0.0546(14) 0.0432(17) -0.0190(14) -0.063(2) O3 0.100(2) 0.0680(17) 0.162(3) 0.0230(18) 0.093(2) 0.0018(15) O4 0.0326(8) 0.0441(10) 0.0443(10) 0.0135(8) -0.0054(7) -0.0047(7) O5 0.106(2) 0.126(3) 0.144(3) 0.060(2) -0.092(2) -0.044(2) O6 0.0827(16) 0.0837(17) 0.0464(12) 0.0303(11) 0.0142(11) 0.0070(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N2 1.701(2) . ? P1 N1 1.704(2) . ? P1 O1 1.7503(18) . ? P1 P2 2.5557(10) . ? P2 N1 1.697(2) . ? P2 N2 1.6977(19) . ? P2 O4 1.7491(17) . ? S1 O3 1.398(3) . ? S1 O2 1.408(3) . ? S1 O1 1.5529(18) . ? S1 C17 1.807(4) . ? S2 O5 1.397(3) . ? S2 O6 1.411(2) . ? S2 O4 1.5508(18) . ? S2 C18 1.830(5) . ? N1 C1 1.443(3) . ? N2 C9 1.441(3) . ? C1 C2 1.400(4) . ? C1 C6 1.400(4) . ? C2 C3 1.393(4) . ? C2 C7 1.507(4) . ? C3 C4 1.386(5) . ? C3 H3 0.9500 . ? C4 C5 1.370(5) . ? C4 H4 0.9500 . ? C5 C6 1.396(4) . ? C5 H5 0.9500 . ? C6 C8 1.506(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.399(3) . ? C9 C14 1.402(3) . ? C10 C11 1.392(3) . ? C10 C15 1.510(3) . ? C11 C12 1.377(4) . ? C11 H11 0.9500 . ? C12 C13 1.385(4) . ? C12 H12 0.9500 . ? C13 C14 1.396(3) . ? C13 H13 0.9500 . ? C14 C16 1.506(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 F1 1.298(5) . ? C17 F3 1.313(5) . ? C17 F2 1.323(4) . ? C18 F6 1.298(4) . ? C18 F4 1.319(4) . ? C18 F5 1.328(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 P1 N1 81.82(9) . . ? N2 P1 O1 100.94(9) . . ? N1 P1 O1 98.42(9) . . ? N2 P1 P2 41.19(6) . . ? N1 P1 P2 41.20(7) . . ? O1 P1 P2 108.15(6) . . ? N1 P2 N2 82.11(9) . . ? N1 P2 O4 100.89(9) . . ? N2 P2 O4 99.36(9) . . ? N1 P2 P1 41.40(6) . . ? N2 P2 P1 41.28(6) . . ? O4 P2 P1 108.81(6) . . ? O3 S1 O2 121.7(2) . . ? O3 S1 O1 109.18(15) . . ? O2 S1 O1 110.84(13) . . ? O3 S1 C17 105.6(2) . . ? O2 S1 C17 107.7(2) . . ? O1 S1 C17 99.33(16) . . ? O5 S2 O6 122.1(2) . . ? O5 S2 O4 108.67(15) . . ? O6 S2 O4 111.13(12) . . ? O5 S2 C18 107.5(2) . . ? O6 S2 C18 105.90(17) . . ? O4 S2 C18 98.87(15) . . ? C1 N1 P2 126.86(16) . . ? C1 N1 P1 130.70(16) . . ? P2 N1 P1 97.41(10) . . ? C9 N2 P2 125.94(14) . . ? C9 N2 P1 133.20(14) . . ? P2 N2 P1 97.53(9) . . ? C2 C1 C6 122.5(2) . . ? C2 C1 N1 119.2(2) . . ? C6 C1 N1 118.3(2) . . ? C3 C2 C1 117.4(3) . . ? C3 C2 C7 120.8(3) . . ? C1 C2 C7 121.8(2) . . ? C4 C3 C2 120.9(3) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C5 C4 C3 120.5(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 121.1(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 117.5(3) . . ? C5 C6 C8 119.8(3) . . ? C1 C6 C8 122.7(2) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C14 122.1(2) . . ? C10 C9 N2 118.63(19) . . ? C14 C9 N2 119.19(19) . . ? C11 C10 C9 117.8(2) . . ? C11 C10 C15 119.8(2) . . ? C9 C10 C15 122.4(2) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C9 117.7(2) . . ? C13 C14 C16 119.8(2) . . ? C9 C14 C16 122.4(2) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? F1 C17 F3 109.1(4) . . ? F1 C17 F2 109.4(3) . . ? F3 C17 F2 109.1(3) . . ? F1 C17 S1 111.1(3) . . ? F3 C17 S1 108.9(3) . . ? F2 C17 S1 109.2(3) . . ? F6 C18 F4 108.9(3) . . ? F6 C18 F5 108.8(4) . . ? F4 C18 F5 109.2(4) . . ? F6 C18 S2 111.0(3) . . ? F4 C18 S2 109.1(3) . . ? F5 C18 S2 109.8(2) . . ? S1 O1 P1 124.60(11) . . ? S2 O4 P2 122.95(11) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.637 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.064 # Attachment 'NB070163_650722.cif' data_nb070163 _database_code_depnum_ccdc_archive 'CCDC 650722' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 F6 N4 O6 P2 S2' _chemical_formula_weight 720.57 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.871(3) _cell_length_b 11.269(4) _cell_length_c 16.513(6) _cell_angle_alpha 75.406(5) _cell_angle_beta 81.369(5) _cell_angle_gamma 86.308(5) _cell_volume 1578.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 5483 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.11 _exptl_crystal_description Rod _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 740 _exptl_absorpt_coefficient_mu 0.351 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8580 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997b)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10866 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0545 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6807 _reflns_number_gt 4850 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0546P)^2^+0.7642P] 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 6807 _refine_ls_number_parameters 421 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0446 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 1.00862(8) 0.69195(6) 0.36739(4) 0.03016(16) Uani 1 1 d . . . P2 P 0.90953(7) 0.85617(6) 0.24733(4) 0.02926(16) Uani 1 1 d . . . N1 N 1.0774(2) 0.78003(19) 0.27108(13) 0.0311(5) Uani 1 1 d . . . N2 N 0.8382(2) 0.74596(19) 0.33532(13) 0.0297(5) Uani 1 1 d . . . C1 C 1.2279(3) 0.8289(2) 0.24151(17) 0.0348(6) Uani 1 1 d . . . C2 C 1.2839(3) 0.9071(3) 0.28324(19) 0.0406(7) Uani 1 1 d . . . C3 C 1.4268(3) 0.9562(3) 0.2518(2) 0.0540(9) Uani 1 1 d . . . H3 H 1.4683 1.0073 0.2802 0.065 Uiso 1 1 calc R . . C4 C 1.5080(3) 0.9317(3) 0.1806(3) 0.0614(10) Uani 1 1 d . . . H4 H 1.6041 0.9680 0.1589 0.074 Uiso 1 1 calc R . . C5 C 1.4519(3) 0.8546(3) 0.1399(3) 0.0599(10) Uani 1 1 d . . . H5 H 1.5105 0.8383 0.0906 0.072 Uiso 1 1 calc R . . C6 C 1.3108(3) 0.8000(3) 0.1697(2) 0.0436(7) Uani 1 1 d . . . C7 C 1.1931(4) 0.9438(3) 0.3581(2) 0.0529(8) Uani 1 1 d . . . H7A H 1.2524 0.9997 0.3769 0.079 Uiso 1 1 calc R . . H7B H 1.1703 0.8704 0.4041 0.079 Uiso 1 1 calc R . . H7C H 1.0976 0.9850 0.3420 0.079 Uiso 1 1 calc R . . C8 C 1.2518(4) 0.7173(3) 0.1232(2) 0.0591(9) Uani 1 1 d . . . H8A H 1.1962 0.6502 0.1640 0.089 Uiso 1 1 calc R . . H8B H 1.3378 0.6833 0.0906 0.089 Uiso 1 1 calc R . . H8C H 1.1832 0.7646 0.0848 0.089 Uiso 1 1 calc R . . C9 C 0.6941(3) 0.7476(2) 0.39047(16) 0.0325(6) Uani 1 1 d . . . C10 C 0.5843(3) 0.6628(3) 0.39240(18) 0.0402(6) Uani 1 1 d . . . C11 C 0.4498(3) 0.6625(3) 0.4487(2) 0.0527(8) Uani 1 1 d . . . H11 H 0.3735 0.6057 0.4515 0.063 Uiso 1 1 calc R . . C12 C 0.4257(4) 0.7428(3) 0.5002(2) 0.0563(9) Uani 1 1 d . . . H12 H 0.3336 0.7408 0.5382 0.068 Uiso 1 1 calc R . . C13 C 0.5344(4) 0.8254(3) 0.49669(19) 0.0500(8) Uani 1 1 d . . . H13 H 0.5164 0.8807 0.5322 0.060 Uiso 1 1 calc R . . C14 C 0.6707(3) 0.8299(3) 0.44212(17) 0.0384(6) Uani 1 1 d . . . C15 C 0.6083(4) 0.5728(3) 0.3383(2) 0.0535(8) Uani 1 1 d . . . H15A H 0.5999 0.6157 0.2796 0.080 Uiso 1 1 calc R . . H15B H 0.5308 0.5099 0.3583 0.080 Uiso 1 1 calc R . . H15C H 0.7099 0.5338 0.3416 0.080 Uiso 1 1 calc R . . C16 C 0.7895(4) 0.9200(3) 0.4424(2) 0.0473(7) Uani 1 1 d . . . H16A H 0.7464 0.9756 0.4774 0.071 Uiso 1 1 calc R . . H16B H 0.8211 0.9675 0.3845 0.071 Uiso 1 1 calc R . . H16C H 0.8782 0.8752 0.4655 0.071 Uiso 1 1 calc R . . N17 N 0.8729(2) 0.80216(18) 0.16029(13) 0.0285(4) Uani 1 1 d . . . C18 C 0.8591(3) 0.8895(2) 0.08692(15) 0.0289(5) Uani 1 1 d . . . H18 H 0.8716 0.9731 0.0856 0.035 Uiso 1 1 calc R . . C19 C 0.8283(3) 0.8612(2) 0.01653(16) 0.0312(5) Uani 1 1 d . . . H19 H 0.8230 0.9243 -0.0335 0.037 Uiso 1 1 calc R . . C20 C 0.8036(3) 0.7367(2) 0.01670(15) 0.0281(5) Uani 1 1 d . . . C21 C 0.8342(3) 0.6466(2) 0.09106(16) 0.0323(6) Uani 1 1 d . . . H21 H 0.8322 0.5619 0.0926 0.039 Uiso 1 1 calc R . . C22 C 0.8661(3) 0.6813(2) 0.15922(16) 0.0328(6) Uani 1 1 d . . . H22 H 0.8844 0.6197 0.2081 0.039 Uiso 1 1 calc R . . N23 N 0.7526(2) 0.70764(19) -0.04705(13) 0.0329(5) Uani 1 1 d . . . C24 C 0.7263(4) 0.8006(3) -0.12358(19) 0.0512(8) Uani 1 1 d . . . H24A H 0.6693 0.8708 -0.1079 0.077 Uiso 1 1 calc R . . H24B H 0.6674 0.7656 -0.1572 0.077 Uiso 1 1 calc R . . H24C H 0.8244 0.8278 -0.1569 0.077 Uiso 1 1 calc R . . C25 C 0.7293(4) 0.5796(3) -0.04635(19) 0.0444(7) Uani 1 1 d . . . H25A H 0.8281 0.5391 -0.0587 0.067 Uiso 1 1 calc R . . H25B H 0.6652 0.5773 -0.0893 0.067 Uiso 1 1 calc R . . H25C H 0.6789 0.5369 0.0094 0.067 Uiso 1 1 calc R . . C26 C 1.2025(4) 0.3810(3) 0.3109(2) 0.0535(8) Uani 1 1 d . . . C27 C 0.7634(5) 0.2474(3) 0.2385(2) 0.0636(10) Uani 1 1 d . . . S1 S 1.07082(8) 0.42395(6) 0.39510(4) 0.03335(16) Uani 1 1 d . . . S2 S 0.76950(19) 0.27053(14) 0.12569(13) 0.0371(3) Uani 0.85 1 d P . . S2' S 0.811(2) 0.255(2) 0.1215(13) 0.123(8) Uani 0.15 1 d P . . O1 O 1.0097(2) 0.54512(16) 0.34282(11) 0.0359(4) Uani 1 1 d . . . O2 O 1.1597(2) 0.44337(17) 0.45532(12) 0.0413(5) Uani 1 1 d . . . O3 O 0.9573(3) 0.33468(19) 0.41849(13) 0.0519(5) Uani 1 1 d . . . O4 O 0.6254(3) 0.3266(3) 0.1103(2) 0.0855(9) Uani 1 1 d . . . O5 O 0.8955(2) 0.3507(2) 0.09135(16) 0.0570(6) Uani 1 1 d . . . O6 O 0.7923(4) 0.1508(2) 0.11289(19) 0.0908(10) Uani 1 1 d . . . F1 F 1.3123(2) 0.4594(3) 0.28262(15) 0.0840(7) Uani 1 1 d . . . F2 F 1.1306(2) 0.37982(19) 0.24644(12) 0.0649(5) Uani 1 1 d . . . F3 F 1.2612(3) 0.2707(2) 0.33932(16) 0.1072(10) Uani 1 1 d . . . F4 F 0.7523(4) 0.3502(2) 0.26113(17) 0.1054(9) Uani 1 1 d . . . F5 F 0.8927(3) 0.1903(2) 0.26539(17) 0.0937(8) Uani 1 1 d . . . F6 F 0.6503(3) 0.1767(3) 0.28136(15) 0.0986(9) 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 P1 0.0379(3) 0.0284(3) 0.0250(3) -0.0071(3) -0.0058(3) -0.0016(3) P2 0.0384(3) 0.0250(3) 0.0255(3) -0.0075(3) -0.0055(3) -0.0014(3) N1 0.0356(11) 0.0297(11) 0.0269(11) -0.0040(9) -0.0051(9) -0.0030(9) N2 0.0355(11) 0.0279(11) 0.0249(11) -0.0056(9) -0.0042(9) 0.0007(9) C1 0.0315(13) 0.0305(14) 0.0390(15) -0.0013(12) -0.0065(11) -0.0015(11) C2 0.0406(14) 0.0324(14) 0.0486(17) -0.0040(13) -0.0158(13) -0.0020(12) C3 0.0370(15) 0.0396(17) 0.085(3) -0.0065(17) -0.0222(17) -0.0039(13) C4 0.0319(15) 0.0402(18) 0.103(3) -0.0060(19) -0.0016(18) -0.0015(13) C5 0.0416(16) 0.0471(19) 0.080(3) -0.0097(18) 0.0138(16) 0.0053(14) C6 0.0391(14) 0.0373(15) 0.0488(18) -0.0064(13) 0.0023(13) 0.0026(12) C7 0.064(2) 0.0508(19) 0.0517(19) -0.0200(16) -0.0157(16) -0.0126(16) C8 0.061(2) 0.061(2) 0.054(2) -0.0247(17) 0.0120(16) -0.0023(17) C9 0.0353(13) 0.0311(13) 0.0269(13) -0.0023(11) -0.0010(10) 0.0036(11) C10 0.0378(14) 0.0390(15) 0.0390(16) 0.0000(13) -0.0061(12) -0.0015(12) C11 0.0388(15) 0.0530(19) 0.055(2) 0.0053(16) -0.0019(14) -0.0046(14) C12 0.0440(17) 0.059(2) 0.051(2) 0.0004(17) 0.0114(15) 0.0103(15) C13 0.0533(18) 0.0485(18) 0.0394(17) -0.0065(14) 0.0068(14) 0.0151(15) C14 0.0437(15) 0.0369(15) 0.0306(14) -0.0043(12) -0.0024(12) 0.0067(12) C15 0.0514(17) 0.0522(19) 0.058(2) -0.0139(16) -0.0027(15) -0.0194(15) C16 0.0608(18) 0.0437(17) 0.0412(17) -0.0225(14) -0.0010(14) 0.0057(14) N17 0.0365(11) 0.0244(10) 0.0253(11) -0.0063(8) -0.0060(9) -0.0007(8) C18 0.0338(12) 0.0232(12) 0.0281(13) -0.0052(10) -0.0005(10) -0.0018(10) C19 0.0396(13) 0.0262(13) 0.0245(12) -0.0022(10) -0.0014(10) -0.0006(10) C20 0.0303(12) 0.0285(13) 0.0254(12) -0.0082(10) -0.0020(10) 0.0014(10) C21 0.0432(14) 0.0227(12) 0.0315(14) -0.0062(10) -0.0075(11) -0.0016(10) C22 0.0460(14) 0.0233(12) 0.0289(13) -0.0041(10) -0.0093(11) 0.0009(11) N23 0.0415(12) 0.0297(11) 0.0287(11) -0.0086(9) -0.0088(9) 0.0038(9) C24 0.084(2) 0.0395(16) 0.0340(16) -0.0084(13) -0.0233(16) 0.0040(16) C25 0.0607(18) 0.0354(15) 0.0435(17) -0.0155(13) -0.0155(14) -0.0048(13) C26 0.062(2) 0.055(2) 0.0461(19) -0.0193(16) -0.0073(16) 0.0120(17) C27 0.078(2) 0.052(2) 0.061(2) -0.0199(18) 0.004(2) -0.0183(19) S1 0.0436(4) 0.0277(3) 0.0292(3) -0.0055(3) -0.0089(3) -0.0012(3) S2 0.0470(6) 0.0240(5) 0.0408(8) -0.0099(5) -0.0028(6) -0.0040(4) S2' 0.170(18) 0.127(13) 0.069(8) -0.045(9) 0.044(10) -0.041(12) O1 0.0498(11) 0.0288(9) 0.0309(10) -0.0076(8) -0.0135(8) 0.0054(8) O2 0.0511(11) 0.0378(11) 0.0377(11) -0.0068(9) -0.0195(9) 0.0017(9) O3 0.0691(14) 0.0446(12) 0.0419(12) -0.0039(10) -0.0101(10) -0.0227(10) O4 0.0557(15) 0.093(2) 0.095(2) 0.0089(17) -0.0219(14) -0.0054(14) O5 0.0500(12) 0.0418(12) 0.0692(16) -0.0038(11) 0.0084(11) -0.0070(10) O6 0.166(3) 0.0364(14) 0.0753(19) -0.0308(14) -0.0028(19) -0.0103(16) F1 0.0489(11) 0.135(2) 0.0708(15) -0.0364(15) 0.0075(10) -0.0128(13) F2 0.0820(13) 0.0770(14) 0.0448(11) -0.0334(10) -0.0082(10) 0.0027(11) F3 0.149(2) 0.0871(18) 0.0812(17) -0.0308(14) -0.0195(16) 0.0747(17) F4 0.163(3) 0.0881(18) 0.0822(18) -0.0565(15) -0.0052(17) -0.0134(17) F5 0.1064(19) 0.0888(18) 0.0844(18) 0.0027(14) -0.0440(15) -0.0156(15) F6 0.1067(18) 0.119(2) 0.0615(15) -0.0104(14) 0.0167(13) -0.0537(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.696(2) . ? P1 N2 1.702(2) . ? P1 O1 1.7994(19) . ? P1 P2 2.5676(11) . ? P2 N1 1.717(2) . ? P2 N2 1.724(2) . ? P2 N17 1.774(2) . ? N1 C1 1.445(3) . ? N2 C9 1.455(3) . ? C1 C6 1.399(4) . ? C1 C2 1.402(4) . ? C2 C3 1.389(4) . ? C2 C7 1.504(5) . ? C3 C4 1.364(5) . ? C3 H3 0.9500 . ? C4 C5 1.381(5) . ? C4 H4 0.9500 . ? C5 C6 1.396(4) . ? C5 H5 0.9500 . ? C6 C8 1.508(5) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C14 1.397(4) . ? C9 C10 1.399(4) . ? C10 C11 1.397(4) . ? C10 C15 1.498(4) . ? C11 C12 1.377(5) . ? C11 H11 0.9500 . ? C12 C13 1.368(5) . ? C12 H12 0.9500 . ? C13 C14 1.391(4) . ? C13 H13 0.9500 . ? C14 C16 1.511(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N17 C18 1.371(3) . ? N17 C22 1.372(3) . ? C18 C19 1.349(4) . ? C18 H18 0.9500 . ? C19 C20 1.433(3) . ? C19 H19 0.9500 . ? C20 N23 1.325(3) . ? C20 C21 1.432(3) . ? C21 C22 1.353(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N23 C24 1.463(4) . ? N23 C25 1.468(3) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 F1 1.309(4) . ? C26 F3 1.316(4) . ? C26 F2 1.323(4) . ? C26 S1 1.820(3) . ? C27 F4 1.298(4) . ? C27 F6 1.322(4) . ? C27 F5 1.356(5) . ? C27 S2 1.808(5) . ? C27 S2' 1.90(2) . ? S1 O3 1.412(2) . ? S1 O2 1.4232(19) . ? S1 O1 1.5347(18) . ? S2 O6 1.415(3) . ? S2 O4 1.418(3) . ? S2 O5 1.438(3) . ? S2' O6 1.24(2) . ? S2' O5 1.30(2) . ? S2' O4 1.80(2) . ? 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 N1 P1 N2 82.30(10) . . ? N1 P1 O1 100.07(10) . . ? N2 P1 O1 97.41(9) . . ? N1 P1 P2 41.52(7) . . ? N2 P1 P2 41.77(7) . . ? O1 P1 P2 108.73(7) . . ? N1 P2 N2 81.07(10) . . ? N1 P2 N17 102.42(10) . . ? N2 P2 N17 104.84(10) . . ? N1 P2 P1 40.92(7) . . ? N2 P2 P1 41.13(7) . . ? N17 P2 P1 114.99(8) . . ? C1 N1 P1 128.87(17) . . ? C1 N1 P2 125.27(17) . . ? P1 N1 P2 97.56(11) . . ? C9 N2 P1 125.58(17) . . ? C9 N2 P2 128.68(17) . . ? P1 N2 P2 97.10(11) . . ? C6 C1 C2 122.0(3) . . ? C6 C1 N1 118.5(2) . . ? C2 C1 N1 119.4(2) . . ? C3 C2 C1 118.3(3) . . ? C3 C2 C7 119.0(3) . . ? C1 C2 C7 122.7(3) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 120.6(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 117.0(3) . . ? C5 C6 C8 120.1(3) . . ? C1 C6 C8 122.9(3) . . ? C2 C7 H7A 109.5 . . ? C2 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C2 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C14 C9 C10 121.7(2) . . ? C14 C9 N2 119.7(2) . . ? C10 C9 N2 118.6(2) . . ? C11 C10 C9 117.5(3) . . ? C11 C10 C15 120.1(3) . . ? C9 C10 C15 122.4(2) . . ? C12 C11 C10 121.4(3) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C9 118.1(3) . . ? C13 C14 C16 119.4(3) . . ? C9 C14 C16 122.4(2) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 N17 C22 118.0(2) . . ? C18 N17 P2 116.38(16) . . ? C22 N17 P2 125.53(17) . . ? C19 C18 N17 122.5(2) . . ? C19 C18 H18 118.8 . . ? N17 C18 H18 118.8 . . ? C18 C19 C20 120.5(2) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? N23 C20 C21 122.4(2) . . ? N23 C20 C19 122.1(2) . . ? C21 C20 C19 115.5(2) . . ? C22 C21 C20 120.4(2) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 N17 122.4(2) . . ? C21 C22 H22 118.8 . . ? N17 C22 H22 118.8 . . ? C20 N23 C24 121.6(2) . . ? C20 N23 C25 121.5(2) . . ? C24 N23 C25 116.8(2) . . ? N23 C24 H24A 109.5 . . ? N23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? N23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N23 C25 H25A 109.5 . . ? N23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? F1 C26 F3 109.5(3) . . ? F1 C26 F2 107.4(3) . . ? F3 C26 F2 108.8(3) . . ? F1 C26 S1 111.1(2) . . ? F3 C26 S1 109.5(2) . . ? F2 C26 S1 110.4(2) . . ? F4 C27 F6 109.2(3) . . ? F4 C27 F5 105.7(3) . . ? F6 C27 F5 105.9(3) . . ? F4 C27 S2 112.2(3) . . ? F6 C27 S2 111.9(3) . . ? F5 C27 S2 111.5(3) . . ? F4 C27 S2' 117.4(7) . . ? F6 C27 S2' 117.3(7) . . ? F5 C27 S2' 99.4(7) . . ? S2 C27 S2' 12.2(7) . . ? O3 S1 O2 120.86(12) . . ? O3 S1 O1 110.63(12) . . ? O2 S1 O1 111.88(11) . . ? O3 S1 C26 105.52(15) . . ? O2 S1 C26 107.16(15) . . ? O1 S1 C26 97.95(13) . . ? O6 S2 O4 115.1(2) . . ? O6 S2 O5 115.2(2) . . ? O4 S2 O5 113.87(18) . . ? O6 S2 C27 103.9(2) . . ? O4 S2 C27 103.3(2) . . ? O5 S2 C27 103.26(18) . . ? O6 S2' O5 142.5(16) . . ? O6 S2' O4 101.9(14) . . ? O5 S2' O4 99.8(13) . . ? O6 S2' C27 106.7(13) . . ? O5 S2' C27 104.7(13) . . ? O4 S2' C27 86.8(8) . . ? S1 O1 P1 125.50(11) . . ? S2 O4 S2' 4.4(7) . . ? S2' O5 S2 15.9(9) . . ? S2' O6 S2 15.8(10) . . ? _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.517 _refine_diff_density_min -0.377 _refine_diff_density_rms 0.059 # Attachment 'RJD192_650811.cif' #============================================================================== data___RJD192 _database_code_depnum_ccdc_archive 'CCDC 650811' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C24 H36 F6 N2 O6 P4 S2 ' _chemical_formula_moiety 'C24 H36 F6 N2 O6 P4 S2 ' _chemical_formula_weight 750.56 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 10.3471(6) _cell_length_b 14.3075(6) _cell_length_c 11.3770(6) _cell_angle_alpha 90.0000 _cell_angle_beta 103.427(3) _cell_angle_gamma 90.0000 _cell_volume 1638.23(15) _cell_formula_units_Z 2 _cell_measurement_reflns_used 22850 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 72.3 _cell_measurement_temperature 123.1 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour paleyellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.521 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776.00 _exptl_absorpt_coefficient_mu 0.433 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 0.925 #============================================================================== # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71070 _diffrn_measurement_device_type 'Rigaku RAXIS-UNKNOWN' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 82596 _diffrn_reflns_av_R_equivalents 0.078 _diffrn_reflns_theta_max 72.41 _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 27 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using reflections with F^2^ > 3.0 sigma(F^2^). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 4761 _reflns_number_gt 4172 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0419 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 4172 _refine_ls_number_parameters 272 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 5.5365 2.9522 2.9337 ; _refine_ls_shift/su_max 0.0020 _refine_diff_density_max 0.57 _refine_diff_density_min -0.56 _refine_ls_extinction_method 'Larson (1970) Crystallographic Computing eq. 22' _refine_ls_extinction_coef 53(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; F F 0.017 0.010 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; P P 0.102 0.094 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S 0.74356(3) 0.35895(2) 0.38172(3) 0.02300(7) Uani 1.00 1 d . . . P(1) P 0.54999(3) 0.08056(2) 0.47993(3) 0.01823(7) Uani 1.00 1 d . . . P(2) P 0.49867(3) 0.08846(2) 0.27384(3) 0.02115(7) Uani 1.00 1 d . . . F(1) F 0.64399(10) 0.51887(6) 0.43158(10) 0.0390(2) Uani 1.00 1 d . . . F(2) F 0.49993(9) 0.40769(7) 0.38702(9) 0.0358(2) Uani 1.00 1 d . . . F(3) F 0.63782(9) 0.40992(7) 0.56069(8) 0.0349(2) Uani 1.00 1 d . . . O(1) O 0.70972(13) 0.38206(9) 0.25526(10) 0.0376(2) Uani 1.00 1 d . . . O(2) O 0.87141(10) 0.39250(8) 0.44830(10) 0.0301(2) Uani 1.00 1 d . . . O(3) O 0.71218(11) 0.26448(7) 0.41016(11) 0.0352(2) Uani 1.00 1 d . . . N(1) N 0.40048(10) 0.03471(7) 0.49911(10) 0.0192(2) Uani 1.00 1 d . . . C(1) C 0.27157(12) 0.07810(8) 0.46672(11) 0.0195(2) Uani 1.00 1 d . . . C(2) C 0.26323(13) 0.17461(9) 0.48974(12) 0.0237(2) Uani 1.00 1 d . . . C(3) C 0.14050(15) 0.21902(11) 0.44768(14) 0.0308(3) Uani 1.00 1 d . . . C(4) C 0.02853(15) 0.17032(12) 0.38958(15) 0.0351(3) Uani 1.00 1 d . . . C(5) C 0.03645(14) 0.07446(12) 0.37476(14) 0.0312(3) Uani 1.00 1 d . . . C(6) C 0.15696(12) 0.02648(9) 0.41308(11) 0.0229(2) Uani 1.00 1 d . . . C(7) C 0.37795(15) 0.23056(10) 0.56081(15) 0.0308(3) Uani 1.00 1 d . . . C(8) C 0.15457(13) -0.07822(10) 0.39726(14) 0.0274(3) Uani 1.00 1 d . . . C(9) C 0.40792(15) -0.01291(10) 0.20734(13) 0.0290(3) Uani 1.00 1 d . . . C(10) C 0.64995(16) 0.09409(12) 0.22339(16) 0.0344(3) Uani 1.00 1 d . . . C(11) C 0.40401(16) 0.19281(10) 0.22828(13) 0.0295(3) Uani 1.00 1 d . . . C(12) C 0.62553(14) 0.42711(10) 0.44355(13) 0.0255(2) Uani 1.00 1 d . . . H(1) H 0.136(2) 0.2868(16) 0.4641(19) 0.045(5) Uiso 1.00 1 c . . . H(2) H -0.059(2) 0.2013(16) 0.363(2) 0.053(6) Uiso 1.00 1 c . . . H(3) H -0.042(2) 0.0406(16) 0.338(2) 0.051(6) Uiso 1.00 1 c . . . H(4) H 0.345(2) 0.2886(16) 0.5853(19) 0.046(5) Uiso 1.00 1 c . . . H(5) H 0.418(2) 0.1988(15) 0.6301(19) 0.040(5) Uiso 1.00 1 c . . . H(6) H 0.4449(19) 0.2449(14) 0.5170(17) 0.035(4) Uiso 1.00 1 c . . . H(7) H 0.065(2) -0.0966(13) 0.3640(18) 0.035(5) Uiso 1.00 1 c . . . H(8) H 0.1868(19) -0.1114(13) 0.4750(17) 0.028(4) Uiso 1.00 1 c . . . H(9) H 0.209(2) -0.0979(14) 0.3384(19) 0.038(5) Uiso 1.00 1 c . . . H(10) H 0.322(2) -0.0121(15) 0.2262(19) 0.041(5) Uiso 1.00 1 c . . . H(11) H 0.453(2) -0.0694(18) 0.239(2) 0.058(6) Uiso 1.00 1 c . . . H(12) H 0.401(2) -0.0093(15) 0.124(2) 0.040(5) Uiso 1.00 1 c . . . H(13) H 0.625(2) 0.0933(15) 0.136(2) 0.049(6) Uiso 1.00 1 c . . . H(14) H 0.698(2) 0.1495(16) 0.256(2) 0.048(6) Uiso 1.00 1 c . . . H(15) H 0.705(2) 0.0395(19) 0.257(2) 0.060(7) Uiso 1.00 1 c . . . H(16) H 0.318(2) 0.1875(16) 0.2499(19) 0.046(5) Uiso 1.00 1 c . . . H(17) H 0.393(2) 0.1997(15) 0.144(2) 0.043(5) Uiso 1.00 1 c . . . H(18) H 0.455(2) 0.2449(17) 0.270(2) 0.054(6) Uiso 1.00 1 c . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.02455(15) 0.02036(15) 0.02446(16) 0.00228(11) 0.00644(11) -0.00179(10) P(1) 0.01751(14) 0.01582(14) 0.02081(15) 0.00057(10) 0.00331(11) 0.00106(10) P(2) 0.02434(16) 0.01911(15) 0.02028(15) 0.00200(11) 0.00572(11) 0.00217(11) F(1) 0.0455(5) 0.0215(4) 0.0553(6) 0.0041(3) 0.0224(4) -0.0031(3) F(2) 0.0223(3) 0.0435(5) 0.0397(5) 0.0041(3) 0.0030(3) -0.0047(3) F(3) 0.0345(4) 0.0464(5) 0.0257(4) 0.0020(3) 0.0111(3) -0.0028(3) O(1) 0.0446(6) 0.0457(6) 0.0231(5) 0.0074(5) 0.0089(4) -0.0016(4) O(2) 0.0236(4) 0.0347(5) 0.0318(5) -0.0016(3) 0.0063(3) -0.0024(4) O(3) 0.0366(5) 0.0199(4) 0.0502(6) 0.0007(4) 0.0120(4) -0.0014(4) N(1) 0.0161(4) 0.0169(4) 0.0243(4) 0.0014(3) 0.0038(3) 0.0020(3) C(1) 0.0182(4) 0.0199(5) 0.0209(5) 0.0041(4) 0.0054(3) 0.0026(4) C(2) 0.0255(5) 0.0204(5) 0.0265(5) 0.0046(4) 0.0087(4) 0.0009(4) C(3) 0.0316(6) 0.0260(6) 0.0359(7) 0.0115(5) 0.0101(5) 0.0032(5) C(4) 0.0267(6) 0.0392(8) 0.0386(7) 0.0142(5) 0.0056(5) 0.0032(6) C(5) 0.0197(5) 0.0388(7) 0.0333(7) 0.0059(5) 0.0026(5) 0.0015(5) C(6) 0.0184(4) 0.0272(6) 0.0227(5) 0.0020(4) 0.0040(4) 0.0012(4) C(7) 0.0321(6) 0.0208(6) 0.0400(7) 0.0023(5) 0.0094(5) -0.0048(5) C(8) 0.0201(5) 0.0268(6) 0.0333(6) -0.0028(4) 0.0019(4) -0.0021(5) C(9) 0.0346(6) 0.0241(6) 0.0256(6) -0.0021(5) 0.0017(5) 0.0020(4) C(10) 0.0333(7) 0.0366(8) 0.0382(7) -0.0052(6) 0.0180(6) -0.0088(6) C(11) 0.0379(7) 0.0237(6) 0.0240(6) 0.0072(5) 0.0012(5) 0.0022(4) C(12) 0.0251(5) 0.0250(5) 0.0266(6) 0.0011(4) 0.0063(4) -0.0022(4) #============================================================================== _computing_data_collection PROCESS _computing_cell_refinement PROCESS _computing_data_reduction CrystalStructure _computing_structure_solution SIR92 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.8' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S(1) O(1) 1.4380(11) yes . . S(1) O(2) 1.4453(10) yes . . S(1) O(3) 1.4442(10) yes . . S(1) C(12) 1.8266(15) yes . . P(1) P(2) 2.2834(4) yes . . P(1) N(1) 1.7401(11) yes . . P(1) N(1) 1.7271(10) yes . 3_656 P(2) C(9) 1.7966(14) yes . . P(2) C(10) 1.7898(18) yes . . P(2) C(11) 1.7948(14) yes . . F(1) C(12) 1.3382(16) yes . . F(2) C(12) 1.3385(15) yes . . F(3) C(12) 1.3319(17) yes . . N(1) C(1) 1.4395(15) yes . . C(1) C(2) 1.4118(17) yes . . C(1) C(6) 1.4100(16) yes . . C(2) C(3) 1.4011(19) yes . . C(2) C(7) 1.5026(18) yes . . C(3) C(4) 1.382(2) yes . . C(4) C(5) 1.387(2) yes . . C(5) C(6) 1.4013(18) yes . . C(6) C(8) 1.5083(19) yes . . C(3) H(1) 0.99(2) no . . C(4) H(2) 0.99(2) no . . C(5) H(3) 0.95(2) no . . C(7) H(4) 0.96(2) no . . C(7) H(5) 0.92(2) no . . C(7) H(6) 0.96(2) no . . C(8) H(7) 0.956(19) no . . C(8) H(8) 0.991(19) no . . C(8) H(9) 1.01(2) no . . C(9) H(10) 0.96(2) no . . C(9) H(11) 0.96(2) no . . C(9) H(12) 0.94(2) no . . C(10) H(13) 0.96(2) no . . C(10) H(14) 0.96(2) no . . C(10) H(15) 0.99(2) no . . C(11) H(16) 0.98(2) no . . C(11) H(17) 0.95(2) no . . C(11) H(18) 0.97(2) no . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O(1) S(1) O(2) 115.38(7) yes . . . O(1) S(1) O(3) 115.10(7) yes . . . O(1) S(1) C(12) 103.49(7) yes . . . O(2) S(1) O(3) 114.80(6) yes . . . O(2) S(1) C(12) 103.49(6) yes . . . O(3) S(1) C(12) 102.02(7) yes . . . P(2) P(1) N(1) 98.39(3) yes . . . P(2) P(1) N(1) 100.36(4) yes . . 3_656 N(1) P(1) N(1) 82.34(5) yes . . 3_656 P(1) P(2) C(9) 111.51(5) yes . . . P(1) P(2) C(10) 108.62(5) yes . . . P(1) P(2) C(11) 108.60(5) yes . . . C(9) P(2) C(10) 108.17(7) yes . . . C(9) P(2) C(11) 110.68(6) yes . . . C(10) P(2) C(11) 109.22(7) yes . . . P(1) N(1) P(1) 97.66(5) yes . . 3_656 P(1) N(1) C(1) 127.10(8) yes . . . P(1) N(1) C(1) 132.44(8) yes 3_656 . . N(1) C(1) C(2) 117.86(10) yes . . . N(1) C(1) C(6) 121.41(10) yes . . . C(2) C(1) C(6) 120.74(11) yes . . . C(1) C(2) C(3) 118.02(11) yes . . . C(1) C(2) C(7) 123.11(11) yes . . . C(3) C(2) C(7) 118.83(12) yes . . . C(2) C(3) C(4) 121.84(14) yes . . . C(3) C(4) C(5) 119.36(13) yes . . . C(4) C(5) C(6) 121.34(12) yes . . . C(1) C(6) C(5) 118.44(12) yes . . . C(1) C(6) C(8) 124.10(10) yes . . . C(5) C(6) C(8) 117.43(11) yes . . . S(1) C(12) F(1) 111.14(11) yes . . . S(1) C(12) F(2) 111.44(9) yes . . . S(1) C(12) F(3) 111.70(9) yes . . . F(1) C(12) F(2) 107.48(11) yes . . . F(1) C(12) F(3) 107.47(11) yes . . . F(2) C(12) F(3) 107.39(12) yes . . . C(2) C(3) H(1) 117.0(11) no . . . C(4) C(3) H(1) 121.1(11) no . . . C(3) C(4) H(2) 121.7(13) no . . . C(5) C(4) H(2) 118.8(13) no . . . C(4) C(5) H(3) 119.3(14) no . . . C(6) C(5) H(3) 119.4(14) no . . . C(2) C(7) H(4) 109.2(12) no . . . C(2) C(7) H(5) 109.9(13) no . . . C(2) C(7) H(6) 114.0(11) no . . . H(4) C(7) H(5) 107.3(19) no . . . H(4) C(7) H(6) 108.0(18) no . . . H(5) C(7) H(6) 108.1(18) no . . . C(6) C(8) H(7) 108.0(12) no . . . C(6) C(8) H(8) 112.2(11) no . . . C(6) C(8) H(9) 111.1(12) no . . . H(7) C(8) H(8) 108.4(17) no . . . H(7) C(8) H(9) 107.6(17) no . . . H(8) C(8) H(9) 109.5(16) no . . . P(2) C(9) H(10) 108.5(12) no . . . P(2) C(9) H(11) 111.0(14) no . . . P(2) C(9) H(12) 107.0(13) no . . . H(10) C(9) H(11) 109(2) no . . . H(10) C(9) H(12) 111.6(17) no . . . H(11) C(9) H(12) 110(2) no . . . P(2) C(10) H(13) 106.3(14) no . . . P(2) C(10) H(14) 108.8(15) no . . . P(2) C(10) H(15) 108.1(16) no . . . H(13) C(10) H(14) 114(2) no . . . H(13) C(10) H(15) 113(2) no . . . H(14) C(10) H(15) 107.2(19) no . . . P(2) C(11) H(16) 109.3(13) no . . . P(2) C(11) H(17) 108.0(13) no . . . P(2) C(11) H(18) 107.3(13) no . . . H(16) C(11) H(17) 111.1(17) no . . . H(16) C(11) H(18) 111(2) no . . . H(17) C(11) H(18) 110(2) no . . . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 O(1) S(1) C(12) F(1) -63.54(10) ? . . . . O(1) S(1) C(12) F(2) 56.32(11) ? . . . . O(1) S(1) C(12) F(3) 176.44(10) ? . . . . O(2) S(1) C(12) F(1) 57.18(10) ? . . . . O(2) S(1) C(12) F(2) 177.04(10) ? . . . . O(2) S(1) C(12) F(3) -62.84(11) ? . . . . O(3) S(1) C(12) F(1) 176.66(9) ? . . . . O(3) S(1) C(12) F(2) -63.49(11) ? . . . . O(3) S(1) C(12) F(3) 56.64(10) ? . . . . P(2) P(1) N(1) P(1) 99.42(4) ? . . . 3_656 P(2) P(1) N(1) C(1) -63.43(10) ? . . . . N(1) P(1) P(2) C(9) -40.68(6) ? . . . . N(1) P(1) P(2) C(10) -159.79(6) ? . . . . N(1) P(1) P(2) C(11) 81.53(6) ? . . . . P(2) P(1) N(1) P(1) -97.18(4) ? . . 3_656 3_656 P(2) P(1) N(1) C(1) 101.41(11) ? . . 3_656 3_656 N(1) P(1) P(2) C(9) 43.00(6) ? 3_656 . . . N(1) P(1) P(2) C(10) -76.11(7) ? 3_656 . . . N(1) P(1) P(2) C(11) 165.21(6) ? 3_656 . . . N(1) P(1) N(1) C(1) -161.41(12) ? . . 3_656 3_656 N(1) P(1) N(1) C(1) -162.84(11) ? 3_656 . . . P(1) N(1) C(1) C(2) -40.91(16) ? . . . . P(1) N(1) C(1) C(6) 138.74(11) ? . . . . P(1) N(1) C(1) C(2) 162.43(10) ? 3_656 . . . P(1) N(1) C(1) C(6) -17.92(19) ? 3_656 . . . N(1) C(1) C(2) C(3) 173.84(13) ? . . . . N(1) C(1) C(2) C(7) -8.5(2) ? . . . . N(1) C(1) C(6) C(5) -174.84(12) ? . . . . N(1) C(1) C(6) C(8) 7.0(2) ? . . . . C(2) C(1) C(6) C(5) 4.8(2) ? . . . . C(2) C(1) C(6) C(8) -173.36(13) ? . . . . C(6) C(1) C(2) C(3) -5.8(2) ? . . . . C(6) C(1) C(2) C(7) 171.84(13) ? . . . . C(1) C(2) C(3) C(4) 2.6(2) ? . . . . C(7) C(2) C(3) C(4) -175.15(15) ? . . . . C(2) C(3) C(4) C(5) 1.6(2) ? . . . . C(3) C(4) C(5) C(6) -2.7(2) ? . . . . C(4) C(5) C(6) C(1) -0.5(2) ? . . . . C(4) C(5) C(6) C(8) 177.78(15) ? . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 P(1) O(3) 3.3150(11) ? . . P(2) O(3) 3.4695(10) ? . . F(1) F(2) 3.0014(15) ? . 3_666 F(1) F(3) 3.1092(14) ? . 3_666 F(1) C(7) 3.5945(16) ? . 3_666 F(1) C(10) 3.249(2) ? . 2_655 F(1) C(12) 3.4975(19) ? . 3_666 F(2) F(1) 3.0014(15) ? . 3_666 F(2) F(3) 3.0966(14) ? . 3_666 F(2) C(8) 3.2643(17) ? . 2_555 F(2) C(11) 3.5869(17) ? . . F(2) C(12) 3.4856(18) ? . 3_666 F(3) F(1) 3.1092(14) ? . 3_666 F(3) F(2) 3.0966(14) ? . 3_666 F(3) C(9) 3.2558(16) ? . 4_555 F(3) C(11) 3.3080(16) ? . 4_555 F(3) C(12) 3.5782(17) ? . 3_666 O(1) C(1) 3.5336(18) ? . 4_554 O(1) C(2) 3.2964(19) ? . 4_554 O(1) C(7) 3.508(2) ? . 4_554 O(1) C(10) 3.348(2) ? . 2_655 O(2) C(9) 3.472(2) ? . 2_655 O(2) C(9) 3.3584(18) ? . 4_555 O(2) C(10) 3.462(2) ? . 2_655 O(2) C(11) 3.3542(18) ? . 4_555 O(3) P(1) 3.3150(11) ? . . O(3) P(2) 3.4695(10) ? . . O(3) C(4) 3.597(2) ? . 1_655 O(3) C(8) 3.5214(17) ? . 3_656 O(3) C(10) 3.200(2) ? . . O(3) C(11) 3.5266(17) ? . . C(1) O(1) 3.5336(18) ? . 4_455 C(2) O(1) 3.2964(19) ? . 4_455 C(4) O(3) 3.597(2) ? . 1_455 C(7) F(1) 3.5945(16) ? . 3_666 C(7) O(1) 3.508(2) ? . 4_455 C(8) F(2) 3.2643(17) ? . 2_545 C(8) O(3) 3.5214(17) ? . 3_656 C(8) C(11) 3.569(2) ? . 2_545 C(9) F(3) 3.2558(16) ? . 4_454 C(9) O(2) 3.472(2) ? . 2_645 C(9) O(2) 3.3584(18) ? . 4_454 C(10) F(1) 3.249(2) ? . 2_645 C(10) O(1) 3.348(2) ? . 2_645 C(10) O(2) 3.462(2) ? . 2_645 C(10) O(3) 3.200(2) ? . . C(11) F(2) 3.5869(17) ? . . C(11) F(3) 3.3080(16) ? . 4_454 C(11) O(2) 3.3542(18) ? . 4_454 C(11) O(3) 3.5266(17) ? . . C(11) C(8) 3.569(2) ? . 2_555 C(12) F(1) 3.4975(19) ? . 3_666 C(12) F(2) 3.4856(18) ? . 3_666 C(12) F(3) 3.5782(17) ? . 3_666 S(1) H(2) 3.08(2) ? . 1_655 S(1) H(12) 3.58(2) ? . 4_555 S(1) H(14) 3.30(2) ? . . S(1) H(15) 3.14(2) ? . 2_655 S(1) H(17) 3.14(2) ? . 4_555 S(1) H(18) 3.38(2) ? . . F(1) H(3) 3.02(2) ? . 2_555 F(1) H(4) 2.76(2) ? . 3_666 F(1) H(6) 3.59(2) ? . 3_666 F(1) H(10) 3.43(2) ? . 4_555 F(1) H(12) 3.029(19) ? . 4_555 F(1) H(13) 2.88(2) ? . 2_655 F(1) H(14) 3.52(2) ? . 2_655 F(1) H(15) 2.95(2) ? . 2_655 F(2) H(3) 3.30(2) ? . 2_555 F(2) H(4) 3.50(2) ? . . F(2) H(6) 2.89(2) ? . . F(2) H(7) 2.78(2) ? . 2_555 F(2) H(9) 2.947(19) ? . 2_555 F(2) H(10) 3.48(2) ? . 2_555 F(2) H(18) 2.67(2) ? . . F(3) H(4) 3.56(2) ? . . F(3) H(6) 3.06(2) ? . . F(3) H(10) 2.77(2) ? . 4_555 F(3) H(12) 3.01(2) ? . 4_555 F(3) H(16) 2.86(2) ? . 4_555 F(3) H(17) 3.03(2) ? . 4_555 O(1) H(2) 3.54(2) ? . 1_655 O(1) H(3) 2.91(2) ? . 2_555 O(1) H(4) 3.60(2) ? . 4_554 O(1) H(5) 3.07(2) ? . 4_554 O(1) H(7) 2.865(19) ? . 2_555 O(1) H(11) 3.54(2) ? . 2_655 O(1) H(13) 3.55(2) ? . 2_655 O(1) H(14) 3.33(2) ? . . O(1) H(15) 2.43(2) ? . 2_655 O(1) H(18) 3.32(2) ? . . O(2) H(1) 3.10(2) ? . 1_655 O(2) H(2) 3.04(2) ? . 1_655 O(2) H(11) 3.15(2) ? . 2_655 O(2) H(12) 3.01(2) ? . 2_655 O(2) H(12) 2.57(2) ? . 4_555 O(2) H(13) 3.03(2) ? . 2_655 O(2) H(13) 2.98(2) ? . 4_555 O(2) H(15) 3.11(2) ? . 2_655 O(2) H(17) 2.55(2) ? . 4_555 O(3) H(2) 2.70(2) ? . 1_655 O(3) H(6) 3.28(2) ? . . O(3) H(8) 2.638(18) ? . 3_656 O(3) H(14) 2.38(2) ? . . O(3) H(17) 2.92(2) ? . 4_555 O(3) H(18) 2.78(2) ? . . C(3) H(13) 3.47(2) ? . 4_455 C(4) H(4) 3.59(2) ? . 4_454 C(4) H(5) 3.46(2) ? . 4_454 C(4) H(7) 3.34(2) ? . 3_556 C(4) H(8) 3.10(2) ? . 3_556 C(4) H(14) 3.42(2) ? . 1_455 C(5) H(7) 3.39(2) ? . 3_556 C(5) H(8) 3.22(2) ? . 3_556 C(5) H(15) 3.41(2) ? . 1_455 C(6) H(3) 3.45(2) ? . 3_556 C(7) H(2) 3.49(2) ? . 4_555 C(8) H(2) 3.58(2) ? . 3_556 C(8) H(3) 3.52(2) ? . 3_556 C(8) H(17) 3.23(2) ? . 2_545 C(8) H(18) 3.21(2) ? . 2_545 C(9) H(1) 3.44(2) ? . 2_545 C(10) H(1) 3.38(2) ? . 4_554 C(10) H(2) 3.42(2) ? . 1_655 C(10) H(3) 3.25(2) ? . 1_655 C(10) H(4) 3.29(2) ? . 4_554 C(11) H(7) 3.23(2) ? . 2_555 C(11) H(9) 3.24(2) ? . 2_555 C(12) H(3) 3.52(2) ? . 2_555 C(12) H(6) 3.42(2) ? . . C(12) H(10) 3.59(2) ? . 4_555 C(12) H(12) 3.317(19) ? . 4_555 C(12) H(15) 3.57(2) ? . 2_655 C(12) H(18) 3.49(2) ? . . H(1) O(2) 3.10(2) ? . 1_455 H(1) C(9) 3.44(2) ? . 2_555 H(1) C(10) 3.38(2) ? . 4_455 H(1) H(11) 3.07(3) ? . 2_555 H(1) H(12) 3.08(3) ? . 2_555 H(1) H(13) 2.63(3) ? . 4_455 H(1) H(14) 3.36(3) ? . 4_455 H(2) S(1) 3.08(2) ? . 1_455 H(2) O(1) 3.54(2) ? . 1_455 H(2) O(2) 3.04(2) ? . 1_455 H(2) O(3) 2.70(2) ? . 1_455 H(2) C(7) 3.49(2) ? . 4_454 H(2) C(8) 3.58(2) ? . 3_556 H(2) C(10) 3.42(2) ? . 1_455 H(2) H(4) 3.09(3) ? . 4_454 H(2) H(5) 2.97(3) ? . 4_454 H(2) H(7) 3.46(3) ? . 3_556 H(2) H(8) 2.82(3) ? . 3_556 H(2) H(14) 2.63(3) ? . 1_455 H(2) H(15) 3.38(3) ? . 1_455 H(3) F(1) 3.02(2) ? . 2_545 H(3) F(2) 3.30(2) ? . 2_545 H(3) O(1) 2.91(2) ? . 2_545 H(3) C(6) 3.45(2) ? . 3_556 H(3) C(8) 3.52(2) ? . 3_556 H(3) C(10) 3.25(2) ? . 1_455 H(3) C(12) 3.52(2) ? . 2_545 H(3) H(7) 3.55(3) ? . 3_556 H(3) H(8) 3.05(3) ? . 3_556 H(3) H(14) 3.06(3) ? . 1_455 H(3) H(15) 2.57(3) ? . 1_455 H(4) F(1) 2.76(2) ? . 3_666 H(4) F(2) 3.50(2) ? . . H(4) F(3) 3.56(2) ? . . H(4) O(1) 3.60(2) ? . 4_455 H(4) C(4) 3.59(2) ? . 4_555 H(4) C(10) 3.29(2) ? . 4_455 H(4) H(2) 3.09(3) ? . 4_555 H(4) H(13) 3.00(3) ? . 4_455 H(4) H(14) 2.88(3) ? . 4_455 H(5) O(1) 3.07(2) ? . 4_455 H(5) C(4) 3.46(2) ? . 4_555 H(5) H(2) 2.97(3) ? . 4_555 H(6) F(1) 3.59(2) ? . 3_666 H(6) F(2) 2.89(2) ? . . H(6) F(3) 3.06(2) ? . . H(6) O(3) 3.28(2) ? . . H(6) C(12) 3.42(2) ? . . H(7) F(2) 2.78(2) ? . 2_545 H(7) O(1) 2.865(19) ? . 2_545 H(7) C(4) 3.34(2) ? . 3_556 H(7) C(5) 3.39(2) ? . 3_556 H(7) C(11) 3.23(2) ? . 2_545 H(7) H(2) 3.46(3) ? . 3_556 H(7) H(3) 3.55(3) ? . 3_556 H(7) H(17) 2.95(2) ? . 2_545 H(7) H(18) 2.71(3) ? . 2_545 H(8) O(3) 2.638(18) ? . 3_656 H(8) C(4) 3.10(2) ? . 3_556 H(8) C(5) 3.22(2) ? . 3_556 H(8) H(2) 2.82(3) ? . 3_556 H(8) H(3) 3.05(3) ? . 3_556 H(8) H(17) 3.05(2) ? . 2_545 H(8) H(18) 3.50(2) ? . 2_545 H(9) F(2) 2.947(19) ? . 2_545 H(9) C(11) 3.24(2) ? . 2_545 H(9) H(16) 3.22(3) ? . 2_545 H(9) H(17) 3.10(3) ? . 2_545 H(9) H(18) 2.92(3) ? . 2_545 H(10) F(1) 3.43(2) ? . 4_454 H(10) F(2) 3.48(2) ? . 2_545 H(10) F(3) 2.77(2) ? . 4_454 H(10) C(12) 3.59(2) ? . 4_454 H(11) O(1) 3.54(2) ? . 2_645 H(11) O(2) 3.15(2) ? . 2_645 H(11) H(1) 3.07(3) ? . 2_545 H(12) S(1) 3.58(2) ? . 4_454 H(12) F(1) 3.029(19) ? . 4_454 H(12) F(3) 3.01(2) ? . 4_454 H(12) O(2) 3.01(2) ? . 2_645 H(12) O(2) 2.57(2) ? . 4_454 H(12) C(12) 3.317(19) ? . 4_454 H(12) H(1) 3.08(3) ? . 2_545 H(12) H(13) 3.15(3) ? . 3_655 H(13) F(1) 2.88(2) ? . 2_645 H(13) O(1) 3.55(2) ? . 2_645 H(13) O(2) 3.03(2) ? . 2_645 H(13) O(2) 2.98(2) ? . 4_454 H(13) C(3) 3.47(2) ? . 4_554 H(13) H(1) 2.63(3) ? . 4_554 H(13) H(4) 3.00(3) ? . 4_554 H(13) H(12) 3.15(3) ? . 3_655 H(14) S(1) 3.30(2) ? . . H(14) F(1) 3.52(2) ? . 2_645 H(14) O(1) 3.33(2) ? . . H(14) O(3) 2.38(2) ? . . H(14) C(4) 3.42(2) ? . 1_655 H(14) H(1) 3.36(3) ? . 4_554 H(14) H(2) 2.63(3) ? . 1_655 H(14) H(3) 3.06(3) ? . 1_655 H(14) H(4) 2.88(3) ? . 4_554 H(15) S(1) 3.14(2) ? . 2_645 H(15) F(1) 2.95(2) ? . 2_645 H(15) O(1) 2.43(2) ? . 2_645 H(15) O(2) 3.11(2) ? . 2_645 H(15) C(5) 3.41(2) ? . 1_655 H(15) C(12) 3.57(2) ? . 2_645 H(15) H(2) 3.38(3) ? . 1_655 H(15) H(3) 2.57(3) ? . 1_655 H(16) F(3) 2.86(2) ? . 4_454 H(16) H(9) 3.22(3) ? . 2_555 H(17) S(1) 3.14(2) ? . 4_454 H(17) F(3) 3.03(2) ? . 4_454 H(17) O(2) 2.55(2) ? . 4_454 H(17) O(3) 2.92(2) ? . 4_454 H(17) C(8) 3.23(2) ? . 2_555 H(17) H(7) 2.95(2) ? . 2_555 H(17) H(8) 3.05(2) ? . 2_555 H(17) H(9) 3.10(3) ? . 2_555 H(18) S(1) 3.38(2) ? . . H(18) F(2) 2.67(2) ? . . H(18) O(1) 3.32(2) ? . . H(18) O(3) 2.78(2) ? . . H(18) C(8) 3.21(2) ? . 2_555 H(18) C(12) 3.49(2) ? . . H(18) H(7) 2.71(3) ? . 2_555 H(18) H(8) 3.50(2) ? . 2_555 H(18) H(9) 2.92(3) ? . 2_555 #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== # Formatted by publCIF