Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2002 data_is2a _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Shevchenko, Igor' ; Institut of Bioorganic Chemistry and Petrochemistry Murmanskaya Street 1 02094 Kiev Ukraine ; 'Andrushko, V.' ; Institut of Bioorganic Chemistry and Petrochemistry Murmanskaya Street 1 02094 Kiev Ukraine ; 'Lork, Enno' ; Institut of Inorganic and Physical Chemistry University of Bremen Leobener Str. D-28359 Bremen Germany ; 'Roschenthaler, Gerd Volker' ; Institut of Inorganic and Physical Chemistry University of Bremen Leobener Str. D-28359 Bremen Germany ; _publ_contact_author 'Dr Igor Shevchenko' _publ_contact_author_address ; Igor Shevchenko Institut of Bioorganic Chemistry and Petrochemistry Murmanskaya Street 1 02094 Kiev Ukraine ; _publ_contact_author_email ishev@bpci.kiev.ua _publ_requested_journal 'Chemical Communications' _publ_section_title ; A novel type of formation of zwitterionic compounds, containing two phosphorus atoms of opposite charge and different coordination number. ; _database_code_CSD 163090 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 115-118 _chemical_formula_moiety ? _chemical_formula_sum 'C19 H36 F7 N3 O P2' _chemical_formula_weight 517.45 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.987(3) _cell_length_b 11.981(3) _cell_length_c 12.436(2) _cell_angle_alpha 99.440(10) _cell_angle_beta 91.68(2) _cell_angle_gamma 110.99(2) _cell_volume 1227.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 3.322 _cell_measurement_theta_max 12.455 _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8662 _exptl_absorpt_correction_T_max 0.9524 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 197 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 'random variation +/-2.0' _diffrn_reflns_number 4497 _diffrn_reflns_av_R_equivalents 0.0586 _diffrn_reflns_av_sigmaI/netI 0.0998 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 23.50 _reflns_number_total 3605 _reflns_number_gt 2328 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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^)+(0.0990P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3605 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1119 _refine_ls_R_factor_gt 0.0688 _refine_ls_wR_factor_ref 0.1748 _refine_ls_wR_factor_gt 0.1560 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.40330(16) 0.21681(10) 0.27951(9) 0.0247(3) Uani 1 1 d . . . N1 N 0.2701(5) 0.0779(3) 0.2474(3) 0.0297(10) Uani 1 1 d . . . C1 C 0.2559(7) -0.0058(4) 0.3266(4) 0.0388(13) Uani 1 1 d . . . H1A H 0.3520 0.0292 0.3801 0.047 Uiso 1 1 calc R . . H1B H 0.2544 -0.0846 0.2862 0.047 Uiso 1 1 calc R . . C2 C 0.1100(8) -0.0287(5) 0.3879(5) 0.0560(17) Uani 1 1 d . . . H2A H 0.1133 0.0481 0.4319 0.067 Uiso 1 1 calc R . . H2B H 0.1074 -0.0862 0.4362 0.067 Uiso 1 1 calc R . . H2C H 0.0139 -0.0631 0.3358 0.067 Uiso 1 1 calc R . . C3 C 0.1390(6) 0.0356(4) 0.1580(4) 0.0366(13) Uani 1 1 d . . . H3A H 0.1508 0.1022 0.1173 0.044 Uiso 1 1 calc R . . H3B H 0.0353 0.0160 0.1901 0.044 Uiso 1 1 calc R . . C4 C 0.1377(8) -0.0748(5) 0.0795(5) 0.0585(18) Uani 1 1 d . . . H4A H 0.2363 -0.0539 0.0427 0.070 Uiso 1 1 calc R . . H4B H 0.0450 -0.1025 0.0248 0.070 Uiso 1 1 calc R . . H4C H 0.1308 -0.1399 0.1199 0.070 Uiso 1 1 calc R . . N2 N 0.5747(5) 0.2034(3) 0.3083(3) 0.0260(9) Uani 1 1 d . . . C5 C 0.6970(7) 0.2853(4) 0.3960(4) 0.0384(13) Uani 1 1 d . . . H5A H 0.6919 0.3674 0.4047 0.046 Uiso 1 1 calc R . . H5B H 0.8040 0.2917 0.3732 0.046 Uiso 1 1 calc R . . C6 C 0.6805(8) 0.2457(6) 0.5057(4) 0.0595(19) Uani 1 1 d . . . H6A H 0.5862 0.2560 0.5366 0.071 Uiso 1 1 calc R . . H6B H 0.7764 0.2955 0.5554 0.071 Uiso 1 1 calc R . . H6C H 0.6682 0.1599 0.4961 0.071 Uiso 1 1 calc R . . C7 C 0.6293(7) 0.1221(5) 0.2315(4) 0.0381(13) Uani 1 1 d . . . H7A H 0.7205 0.1723 0.1963 0.046 Uiso 1 1 calc R . . H7B H 0.5415 0.0746 0.1733 0.046 Uiso 1 1 calc R . . C8 C 0.6810(8) 0.0337(5) 0.2844(5) 0.0518(16) Uani 1 1 d . . . H8A H 0.7750 0.0796 0.3369 0.062 Uiso 1 1 calc R . . H8B H 0.7078 -0.0212 0.2276 0.062 Uiso 1 1 calc R . . H8C H 0.5933 -0.0139 0.3225 0.062 Uiso 1 1 calc R . . C9 C 0.3627(6) 0.3051(4) 0.3981(4) 0.0302(12) Uani 1 1 d . . . H9A H 0.4625 0.3753 0.4266 0.036 Uiso 1 1 calc R . . H9B H 0.3348 0.2544 0.4552 0.036 Uiso 1 1 calc R . . P2 P 0.20028(16) 0.36428(11) 0.37810(10) 0.0296(4) Uani 1 1 d . . . H2 H 0.075(6) 0.401(4) 0.367(4) 0.036 Uiso 1 1 d . . . F1 F 0.0646(3) 0.2338(2) 0.3920(2) 0.0409(8) Uani 1 1 d . . . F2 F 0.2222(4) 0.4144(3) 0.5115(2) 0.0425(8) Uani 1 1 d . . . F3 F 0.3330(4) 0.4953(2) 0.3601(2) 0.0394(8) Uani 1 1 d . . . O1 O 0.1650(4) 0.3125(3) 0.2342(2) 0.0329(8) Uani 1 1 d . . . C10 C 0.2792(6) 0.3346(4) 0.1636(4) 0.0281(11) Uani 1 1 d . . . C11 C 0.2482(7) 0.4016(5) 0.0779(4) 0.0394(14) Uani 1 1 d . . . H11A H 0.3320 0.4133 0.0275 0.047 Uiso 1 1 calc R . . H11B H 0.2489 0.4810 0.1137 0.047 Uiso 1 1 calc R . . H11C H 0.1437 0.3539 0.0370 0.047 Uiso 1 1 calc R . . C12 C 0.4005(6) 0.2950(4) 0.1689(3) 0.0240(11) Uani 1 1 d . . . C13 C 0.5234(6) 0.3089(4) 0.0900(3) 0.0256(10) Uani 1 1 d . . . C14 C 0.4773(7) 0.2250(4) -0.0174(4) 0.0350(12) Uani 1 1 d . . . F4 F 0.3189(4) 0.1798(3) -0.0458(2) 0.0478(8) Uani 1 1 d . . . F5 F 0.5174(5) 0.1260(3) -0.0233(2) 0.0610(10) Uani 1 1 d . . . F6 F 0.5426(4) 0.2761(3) -0.1027(2) 0.0569(10) Uani 1 1 d . . . C15 C 0.6777(6) 0.3862(4) 0.1131(4) 0.0274(11) Uani 1 1 d . . . F7 F 0.7877(4) 0.3630(3) 0.0501(2) 0.0399(8) Uani 1 1 d . . . N3 N 0.7470(5) 0.4868(3) 0.1900(3) 0.0306(10) Uani 1 1 d . . . C16 C 0.9104(6) 0.5140(5) 0.2404(4) 0.0334(12) Uani 1 1 d . . . H16A H 0.9324 0.4379 0.2296 0.040 Uiso 1 1 calc R . . H16B H 0.9141 0.5420 0.3203 0.040 Uiso 1 1 calc R . . C17 C 1.0426(7) 0.6102(5) 0.1948(5) 0.0448(14) Uani 1 1 d . . . H17A H 1.0362 0.5859 0.1151 0.054 Uiso 1 1 calc R . . H17B H 1.1472 0.6179 0.2274 0.054 Uiso 1 1 calc R . . H17C H 1.0292 0.6886 0.2126 0.054 Uiso 1 1 calc R . . C18 C 0.6502(6) 0.5531(4) 0.2415(4) 0.0335(12) Uani 1 1 d . . . H18A H 0.6127 0.5219 0.3087 0.040 Uiso 1 1 calc R . . H18B H 0.5544 0.5362 0.1908 0.040 Uiso 1 1 calc R . . C19 C 0.7393(7) 0.6902(4) 0.2714(4) 0.0400(13) Uani 1 1 d . . . H19A H 0.8317 0.7081 0.3242 0.048 Uiso 1 1 calc R . . H19B H 0.6674 0.7286 0.3041 0.048 Uiso 1 1 calc R . . H19C H 0.7761 0.7221 0.2053 0.048 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0315(8) 0.0177(6) 0.0254(6) 0.0077(5) 0.0007(5) 0.0083(6) N1 0.036(3) 0.018(2) 0.034(2) 0.0105(16) -0.0043(19) 0.0077(19) C1 0.049(4) 0.023(3) 0.043(3) 0.014(2) 0.000(3) 0.009(3) C2 0.060(4) 0.041(3) 0.074(4) 0.036(3) 0.015(4) 0.016(3) C3 0.038(3) 0.028(3) 0.039(3) 0.008(2) -0.011(2) 0.007(2) C4 0.082(5) 0.032(3) 0.049(3) -0.001(3) -0.031(3) 0.013(3) N2 0.029(2) 0.021(2) 0.026(2) 0.0063(16) -0.0011(18) 0.0076(19) C5 0.040(3) 0.024(3) 0.051(3) 0.002(2) -0.011(3) 0.015(3) C6 0.087(5) 0.063(4) 0.042(3) -0.003(3) -0.021(3) 0.052(4) C7 0.044(3) 0.042(3) 0.035(3) 0.006(2) -0.003(3) 0.025(3) C8 0.061(4) 0.037(3) 0.059(4) -0.001(3) -0.006(3) 0.025(3) C9 0.033(3) 0.028(3) 0.030(3) 0.010(2) 0.000(2) 0.010(2) P2 0.0342(8) 0.0265(7) 0.0301(7) 0.0079(5) 0.0028(6) 0.0124(6) F1 0.0376(19) 0.0359(17) 0.0494(17) 0.0182(13) 0.0060(14) 0.0090(15) F2 0.055(2) 0.0457(18) 0.0320(16) 0.0055(13) 0.0059(14) 0.0253(16) F3 0.050(2) 0.0213(14) 0.0475(17) 0.0103(12) 0.0064(15) 0.0117(14) O1 0.036(2) 0.0347(19) 0.0296(18) 0.0080(14) -0.0004(16) 0.0150(17) C10 0.037(3) 0.018(2) 0.026(3) 0.0041(19) -0.004(2) 0.006(2) C11 0.061(4) 0.039(3) 0.032(3) 0.017(2) 0.000(3) 0.031(3) C12 0.027(3) 0.016(2) 0.027(2) 0.0072(18) -0.004(2) 0.004(2) C13 0.036(3) 0.023 0.023(2) 0.0097(18) 0.001(2) 0.014(2) C14 0.044(4) 0.031(3) 0.032(3) 0.010(2) 0.005(3) 0.015(3) F4 0.054(2) 0.0481(19) 0.0332(16) -0.0033(14) -0.0051(15) 0.0150(17) F5 0.097(3) 0.0435(19) 0.0476(19) -0.0086(14) -0.0139(18) 0.040(2) F6 0.078(3) 0.051(2) 0.0268(16) 0.0097(14) 0.0100(16) 0.0044(19) C15 0.034(3) 0.029(3) 0.024(2) 0.014(2) 0.004(2) 0.012(2) F7 0.0452(19) 0.0395(17) 0.0364(16) 0.0098(12) 0.0116(14) 0.0155(15) N3 0.036(3) 0.020(2) 0.032(2) 0.0087(17) -0.0005(19) 0.0055(19) C16 0.031(3) 0.037(3) 0.033(3) 0.011(2) 0.002(2) 0.012(3) C17 0.043(4) 0.039(3) 0.049(3) 0.011(2) 0.005(3) 0.010(3) C18 0.039(3) 0.025(3) 0.036(3) 0.007(2) -0.002(2) 0.010(2) C19 0.049(4) 0.021(3) 0.044(3) 0.005(2) -0.004(3) 0.007(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 N1 1.640(4) . ? P1 N2 1.640(4) . ? P1 C12 1.792(4) . ? P1 C9 1.796(5) . ? N1 C3 1.480(6) . ? N1 C1 1.494(6) . ? C1 C2 1.498(8) . ? C3 C4 1.506(7) . ? N2 C5 1.472(6) . ? N2 C7 1.472(6) . ? C5 C6 1.510(7) . ? C7 C8 1.527(7) . ? C9 P2 1.863(5) . ? P2 F1 1.642(3) . ? P2 F2 1.649(3) . ? P2 F3 1.651(3) . ? P2 O1 1.774(3) . ? O1 C10 1.353(6) . ? C10 C12 1.339(7) . ? C10 C11 1.510(6) . ? C12 C13 1.482(6) . ? C13 C15 1.354(7) . ? C13 C14 1.481(6) . ? C14 F4 1.342(6) . ? C14 F5 1.350(6) . ? C14 F6 1.355(6) . ? C15 N3 1.344(6) . ? C15 F7 1.356(5) . ? N3 C18 1.470(6) . ? N3 C16 1.480(6) . ? C16 C17 1.528(7) . ? C18 C19 1.522(6) . ? 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 106.3(2) . . ? N1 P1 C12 109.0(2) . . ? N2 P1 C12 114.7(2) . . ? N1 P1 C9 113.1(2) . . ? N2 P1 C9 107.7(2) . . ? C12 P1 C9 106.2(2) . . ? C3 N1 C1 115.6(4) . . ? C3 N1 P1 124.9(3) . . ? C1 N1 P1 118.2(3) . . ? N1 C1 C2 114.3(4) . . ? N1 C3 C4 112.5(4) . . ? C5 N2 C7 114.6(4) . . ? C5 N2 P1 124.3(3) . . ? C7 N2 P1 120.0(3) . . ? N2 C5 C6 114.6(5) . . ? N2 C7 C8 114.3(4) . . ? P1 C9 P2 116.5(3) . . ? F1 P2 F2 91.14(16) . . ? F1 P2 F3 177.93(17) . . ? F2 P2 F3 90.49(16) . . ? F1 P2 O1 88.14(16) . . ? F2 P2 O1 176.21(17) . . ? F3 P2 O1 90.16(16) . . ? F1 P2 C9 90.67(19) . . ? F2 P2 C9 88.03(18) . . ? F3 P2 C9 90.66(19) . . ? O1 P2 C9 95.70(18) . . ? C10 O1 P2 124.9(3) . . ? C12 C10 O1 122.1(4) . . ? C12 C10 C11 125.4(5) . . ? O1 C10 C11 112.4(4) . . ? C10 C12 C13 124.9(4) . . ? C10 C12 P1 114.8(4) . . ? C13 C12 P1 120.3(3) . . ? C15 C13 C14 118.1(4) . . ? C15 C13 C12 124.2(4) . . ? C14 C13 C12 117.5(4) . . ? F4 C14 F5 104.5(4) . . ? F4 C14 F6 104.8(4) . . ? F5 C14 F6 104.3(4) . . ? F4 C14 C13 113.0(4) . . ? F5 C14 C13 114.7(4) . . ? F6 C14 C13 114.4(4) . . ? N3 C15 C13 131.4(4) . . ? N3 C15 F7 110.8(4) . . ? C13 C15 F7 117.7(4) . . ? C15 N3 C18 120.0(4) . . ? C15 N3 C16 119.3(4) . . ? C18 N3 C16 119.2(4) . . ? N3 C16 C17 114.4(4) . . ? N3 C18 C19 113.8(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 P1 N1 C3 -140.1(4) . . . . ? C12 P1 N1 C3 -16.0(4) . . . . ? C9 P1 N1 C3 101.9(4) . . . . ? N2 P1 N1 C1 53.7(4) . . . . ? C12 P1 N1 C1 177.8(3) . . . . ? C9 P1 N1 C1 -64.3(4) . . . . ? C3 N1 C1 C2 -61.4(6) . . . . ? P1 N1 C1 C2 106.1(5) . . . . ? C1 N1 C3 C4 -67.3(6) . . . . ? P1 N1 C3 C4 126.1(4) . . . . ? N1 P1 N2 C5 -142.3(4) . . . . ? C12 P1 N2 C5 97.3(4) . . . . ? C9 P1 N2 C5 -20.7(4) . . . . ? N1 P1 N2 C7 50.5(4) . . . . ? C12 P1 N2 C7 -70.0(4) . . . . ? C9 P1 N2 C7 172.0(4) . . . . ? C7 N2 C5 C6 -101.8(5) . . . . ? P1 N2 C5 C6 90.4(5) . . . . ? C5 N2 C7 C8 61.9(6) . . . . ? P1 N2 C7 C8 -129.7(4) . . . . ? N1 P1 C9 P2 -76.4(3) . . . . ? N2 P1 C9 P2 166.4(2) . . . . ? C12 P1 C9 P2 43.1(3) . . . . ? P1 C9 P2 F1 83.3(3) . . . . ? P1 C9 P2 F2 174.4(3) . . . . ? P1 C9 P2 F3 -95.1(3) . . . . ? P1 C9 P2 O1 -4.9(3) . . . . ? F1 P2 O1 C10 -142.1(3) . . . . ? F2 P2 O1 C10 139(3) . . . . ? F3 P2 O1 C10 39.0(3) . . . . ? C9 P2 O1 C10 -51.6(4) . . . . ? P2 O1 C10 C12 61.8(5) . . . . ? P2 O1 C10 C11 -120.9(4) . . . . ? O1 C10 C12 C13 175.8(4) . . . . ? C11 C10 C12 C13 -1.1(7) . . . . ? O1 C10 C12 P1 -2.4(6) . . . . ? C11 C10 C12 P1 -179.3(4) . . . . ? N1 P1 C12 C10 77.9(4) . . . . ? N2 P1 C12 C10 -163.1(3) . . . . ? C9 P1 C12 C10 -44.3(4) . . . . ? N1 P1 C12 C13 -100.4(4) . . . . ? N2 P1 C12 C13 18.6(4) . . . . ? C9 P1 C12 C13 137.4(4) . . . . ? C10 C12 C13 C15 108.2(6) . . . . ? P1 C12 C13 C15 -73.7(5) . . . . ? C10 C12 C13 C14 -77.4(6) . . . . ? P1 C12 C13 C14 100.7(4) . . . . ? C15 C13 C14 F4 -161.2(4) . . . . ? C12 C13 C14 F4 24.0(6) . . . . ? C15 C13 C14 F5 79.1(6) . . . . ? C12 C13 C14 F5 -95.7(5) . . . . ? C15 C13 C14 F6 -41.4(6) . . . . ? C12 C13 C14 F6 143.8(4) . . . . ? C14 C13 C15 N3 164.1(5) . . . . ? C12 C13 C15 N3 -21.6(8) . . . . ? C14 C13 C15 F7 -15.7(6) . . . . ? C12 C13 C15 F7 158.6(4) . . . . ? C13 C15 N3 C18 -21.0(7) . . . . ? F7 C15 N3 C18 158.8(4) . . . . ? C13 C15 N3 C16 144.9(5) . . . . ? F7 C15 N3 C16 -35.3(5) . . . . ? C15 N3 C16 C17 101.0(5) . . . . ? C18 N3 C16 C17 -93.0(5) . . . . ? C15 N3 C18 C19 -146.4(4) . . . . ? C16 N3 C18 C19 47.7(6) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.731 _refine_diff_density_min -0.533 _refine_diff_density_rms 0.090