# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ww87 _database_code_depnum_ccdc_archive 'CCDC 907697' #TrackingRef 'ww87.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_absolute_configuration ad _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 Cl F3 N2 O5 P' _chemical_formula_sum 'C19 H19 Cl F3 N2 O5 P' _chemical_formula_weight 478.78 _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.6899(10) _cell_length_b 10.8171(12) _cell_length_c 19.580(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2052.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 228(2) _cell_measurement_reflns_used 9208 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 32.76 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.550 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.326 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8333 _exptl_absorpt_correction_T_max 0.8830 _exptl_absorpt_process_details Bruker,SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 228(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 61965 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0145 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 32.88 _reflns_number_total 7620 _reflns_number_gt 7058 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0451P)^2^+0.1939P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(4) _refine_ls_number_reflns 7620 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0774 _refine_ls_wR_factor_gt 0.0746 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _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 Cl1 Cl 0.82451(4) 0.02656(4) 0.221020(19) 0.04913(9) Uani 1 1 d . . . P1 P 0.49677(2) -0.27074(2) 0.067800(14) 0.02417(5) Uani 1 1 d . . . O1 O 0.18010(9) 0.02979(9) -0.02949(5) 0.03612(18) Uani 1 1 d . . . O2 O 0.62016(8) -0.22993(8) 0.03057(5) 0.03452(17) Uani 1 1 d . . . O3 O 0.39592(8) -0.35567(7) 0.02706(4) 0.02882(15) Uani 1 1 d . . . O4 O 0.52282(11) -0.33589(8) 0.13728(5) 0.0419(2) Uani 1 1 d . . . O5 O -0.10045(12) 0.47221(11) 0.18492(6) 0.0491(2) Uani 1 1 d . . . F1 F 0.20106(8) -0.06465(8) 0.15827(4) 0.04211(18) Uani 1 1 d . . . F2 F 0.21340(8) -0.25986(8) 0.13876(4) 0.04176(18) Uani 1 1 d . . . F3 F 0.35220(9) -0.17444(8) 0.21062(4) 0.04354(19) Uani 1 1 d . . . N1 N 0.31183(9) -0.10246(8) 0.03115(5) 0.02417(15) Uani 1 1 d . . . H1N H 0.264(2) -0.1627(17) 0.0137(9) 0.047(5) Uiso 1 1 d . . . N2 N 0.34147(10) 0.11178(8) 0.04221(5) 0.02616(16) Uani 1 1 d . . . C1 C 0.68001(11) 0.05506(11) 0.17118(5) 0.0300(2) Uani 1 1 d . . . C2 C 0.59724(10) -0.04354(10) 0.15303(5) 0.02634(18) Uani 1 1 d . . . H2 H 0.6181 -0.1233 0.1690 0.032 Uiso 1 1 calc R . . C3 C 0.48290(9) -0.02515(9) 0.11105(5) 0.02163(15) Uani 1 1 d . . . C4 C 0.39101(9) -0.13296(9) 0.09160(5) 0.02125(16) Uani 1 1 d . . . C5 C 0.27204(10) 0.01421(10) 0.01284(5) 0.02499(17) Uani 1 1 d . . . C6 C 0.45187(10) 0.09385(9) 0.08727(5) 0.02303(16) Uani 1 1 d . . . C7 C 0.53487(13) 0.19261(10) 0.10850(6) 0.0305(2) Uani 1 1 d . . . H7 H 0.5129 0.2733 0.0944 0.037 Uiso 1 1 calc R . . C8 C 0.64886(12) 0.17337(11) 0.14991(6) 0.0325(2) Uani 1 1 d . . . H8 H 0.7044 0.2403 0.1634 0.039 Uiso 1 1 calc R . . C9 C 0.28960(11) -0.15921(10) 0.15078(6) 0.0287(2) Uani 1 1 d . . . C10 C 0.41794(13) -0.38758(13) -0.04405(6) 0.0362(2) Uani 1 1 d . . . H10A H 0.4778 -0.3266 -0.0651 0.054 Uiso 1 1 calc R . . H10B H 0.3300 -0.3890 -0.0677 0.054 Uiso 1 1 calc R . . H10C H 0.4608 -0.4685 -0.0469 0.054 Uiso 1 1 calc R . . C11 C 0.49194(18) -0.46163(12) 0.15586(7) 0.0465(3) Uani 1 1 d . . . H11A H 0.3964 -0.4797 0.1450 0.070 Uiso 1 1 calc R . . H11B H 0.5069 -0.4727 0.2045 0.070 Uiso 1 1 calc R . . H11C H 0.5517 -0.5172 0.1306 0.070 Uiso 1 1 calc R . . C12 C 0.30195(12) 0.23567(11) 0.01877(6) 0.0299(2) Uani 1 1 d . . . H12A H 0.2634 0.2292 -0.0274 0.036 Uiso 1 1 calc R . . H12B H 0.3849 0.2873 0.0161 0.036 Uiso 1 1 calc R . . C13 C 0.19735(11) 0.29896(9) 0.06459(6) 0.02695(18) Uani 1 1 d . . . C14 C 0.13143(15) 0.23960(12) 0.11845(7) 0.0397(3) Uani 1 1 d . . . H14 H 0.1546 0.1573 0.1288 0.048 Uiso 1 1 calc R . . C15 C 0.03219(16) 0.29949(13) 0.15708(7) 0.0435(3) Uani 1 1 d . . . H15 H -0.0116 0.2576 0.1931 0.052 Uiso 1 1 calc R . . C16 C -0.00294(13) 0.42112(11) 0.14282(6) 0.0342(2) Uani 1 1 d . . . C17 C 0.06055(12) 0.48210(11) 0.08916(6) 0.0322(2) Uani 1 1 d . . . H17 H 0.0368 0.5642 0.0788 0.039 Uiso 1 1 calc R . . C18 C 0.15978(12) 0.42053(10) 0.05084(6) 0.0290(2) Uani 1 1 d . . . H18 H 0.2028 0.4623 0.0145 0.035 Uiso 1 1 calc R . . C19 C -0.13422(17) 0.59856(16) 0.17470(9) 0.0516(4) Uani 1 1 d . . . H19A H -0.0523 0.6489 0.1811 0.077 Uiso 1 1 calc R . . H19B H -0.2043 0.6232 0.2074 0.077 Uiso 1 1 calc R . . H19C H -0.1691 0.6099 0.1287 0.077 Uiso 1 1 calc R . . _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 Cl1 0.04200(15) 0.05319(19) 0.05221(19) -0.00010(15) -0.02559(14) -0.00762(14) P1 0.02031(9) 0.02072(10) 0.03148(12) -0.00229(9) -0.00095(9) 0.00039(8) O1 0.0339(4) 0.0367(4) 0.0377(4) 0.0026(3) -0.0126(3) 0.0029(3) O2 0.0225(3) 0.0303(4) 0.0508(5) -0.0105(4) 0.0081(3) -0.0021(3) O3 0.0265(3) 0.0278(3) 0.0322(4) -0.0062(3) 0.0019(3) -0.0053(3) O4 0.0584(6) 0.0253(4) 0.0419(5) 0.0031(3) -0.0179(4) 0.0049(4) O5 0.0490(5) 0.0525(6) 0.0458(5) -0.0019(5) 0.0105(4) 0.0155(5) F1 0.0393(4) 0.0410(4) 0.0461(4) 0.0018(3) 0.0190(3) 0.0105(3) F2 0.0368(4) 0.0386(4) 0.0499(4) 0.0036(3) 0.0094(3) -0.0139(3) F3 0.0473(4) 0.0574(5) 0.0259(3) 0.0098(3) 0.0025(3) -0.0031(4) N1 0.0227(3) 0.0242(4) 0.0255(4) -0.0017(3) -0.0045(3) -0.0007(3) N2 0.0281(4) 0.0225(4) 0.0278(4) 0.0015(3) -0.0034(3) 0.0020(3) C1 0.0284(4) 0.0361(5) 0.0254(4) -0.0040(4) -0.0046(4) -0.0037(4) C2 0.0258(4) 0.0279(4) 0.0253(4) -0.0007(4) -0.0044(3) -0.0004(3) C3 0.0219(4) 0.0218(4) 0.0212(4) -0.0006(3) -0.0002(3) -0.0011(3) C4 0.0196(3) 0.0214(4) 0.0228(4) 0.0005(3) 0.0003(3) -0.0005(3) C5 0.0240(4) 0.0263(4) 0.0247(4) -0.0003(3) -0.0003(3) 0.0011(3) C6 0.0245(4) 0.0223(4) 0.0223(4) -0.0013(3) 0.0001(3) 0.0001(3) C7 0.0370(5) 0.0223(4) 0.0322(5) -0.0028(4) -0.0022(4) -0.0032(4) C8 0.0346(5) 0.0309(5) 0.0319(5) -0.0079(4) -0.0026(4) -0.0085(4) C9 0.0276(4) 0.0288(5) 0.0296(5) 0.0029(4) 0.0051(4) -0.0010(4) C10 0.0308(5) 0.0443(6) 0.0334(5) -0.0107(5) 0.0000(4) 0.0006(4) C11 0.0623(8) 0.0348(6) 0.0425(7) 0.0109(5) 0.0108(6) -0.0004(6) C12 0.0335(5) 0.0246(4) 0.0317(5) 0.0059(4) 0.0001(4) 0.0043(4) C13 0.0277(4) 0.0234(4) 0.0298(4) 0.0025(4) -0.0036(4) 0.0009(3) C14 0.0502(7) 0.0278(5) 0.0410(6) 0.0101(5) 0.0088(5) 0.0062(5) C15 0.0511(7) 0.0376(6) 0.0418(6) 0.0086(5) 0.0133(6) 0.0044(5) C16 0.0321(5) 0.0362(5) 0.0343(5) -0.0025(4) -0.0018(4) 0.0053(5) C17 0.0340(5) 0.0254(5) 0.0372(5) 0.0007(4) -0.0056(4) 0.0040(4) C18 0.0307(5) 0.0228(4) 0.0336(5) 0.0045(4) -0.0027(4) -0.0004(4) C19 0.0455(7) 0.0548(8) 0.0544(8) -0.0127(7) -0.0043(6) 0.0196(6) _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. ; _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C1 1.7343(11) . ? P1 O2 1.4683(8) . ? P1 O4 1.5528(9) . ? P1 O3 1.5605(8) . ? P1 C4 1.8677(10) . ? O1 C5 1.2284(12) . ? O3 C10 1.4503(14) . ? O4 C11 1.4394(15) . ? O5 C16 1.3701(15) . ? O5 C19 1.420(2) . ? F1 C9 1.3431(13) . ? F2 C9 1.3364(13) . ? F3 C9 1.3296(14) . ? N1 C5 1.3674(13) . ? N1 C4 1.4486(13) . ? N1 H1N 0.87(2) . ? N2 C5 1.3775(13) . ? N2 C6 1.4002(13) . ? N2 C12 1.4674(14) . ? C1 C8 1.3793(17) . ? C1 C2 1.3810(15) . ? C2 C3 1.3939(13) . ? C2 H2 0.9400 . ? C3 C6 1.4014(13) . ? C3 C4 1.5158(13) . ? C4 C9 1.5457(14) . ? C6 C7 1.4003(14) . ? C7 C8 1.3859(17) . ? C7 H7 0.9400 . ? C8 H8 0.9400 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C12 C13 1.5169(15) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 C14 1.3902(16) . ? C13 C18 1.3908(14) . ? C14 C15 1.3844(18) . ? C14 H14 0.9400 . ? C15 C16 1.3874(18) . ? C15 H15 0.9400 . ? C16 C17 1.3847(17) . ? C17 C18 1.3896(16) . ? C17 H17 0.9400 . ? C18 H18 0.9400 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 P1 O4 116.05(6) . . ? O2 P1 O3 115.67(5) . . ? O4 P1 O3 106.40(5) . . ? O2 P1 C4 109.31(5) . . ? O4 P1 C4 103.46(5) . . ? O3 P1 C4 104.69(4) . . ? C10 O3 P1 122.59(8) . . ? C11 O4 P1 128.06(9) . . ? C16 O5 C19 117.55(12) . . ? C5 N1 C4 125.01(9) . . ? C5 N1 H1N 116.1(13) . . ? C4 N1 H1N 115.6(12) . . ? C5 N2 C6 122.01(8) . . ? C5 N2 C12 116.21(9) . . ? C6 N2 C12 121.54(9) . . ? C8 C1 C2 120.78(10) . . ? C8 C1 Cl1 120.76(9) . . ? C2 C1 Cl1 118.45(9) . . ? C1 C2 C3 120.21(10) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C2 C3 C6 119.83(9) . . ? C2 C3 C4 120.35(8) . . ? C6 C3 C4 119.81(8) . . ? N1 C4 C3 109.95(8) . . ? N1 C4 C9 108.52(8) . . ? C3 C4 C9 109.05(8) . . ? N1 C4 P1 105.58(6) . . ? C3 C4 P1 110.75(6) . . ? C9 C4 P1 112.91(7) . . ? O1 C5 N1 120.53(10) . . ? O1 C5 N2 122.06(10) . . ? N1 C5 N2 117.39(9) . . ? N2 C6 C7 121.34(9) . . ? N2 C6 C3 120.03(8) . . ? C7 C6 C3 118.62(9) . . ? C8 C7 C6 121.12(10) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C1 C8 C7 119.37(10) . . ? C1 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? F3 C9 F2 107.84(9) . . ? F3 C9 F1 106.83(10) . . ? F2 C9 F1 106.67(9) . . ? F3 C9 C4 113.16(9) . . ? F2 C9 C4 111.65(9) . . ? F1 C9 C4 110.37(9) . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 H11A 109.5 . . ? O4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 113.67(9) . . ? N2 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? N2 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C14 C13 C18 117.60(10) . . ? C14 C13 C12 123.18(10) . . ? C18 C13 C12 119.16(10) . . ? C15 C14 C13 121.16(11) . . ? C15 C14 H14 119.4 . . ? C13 C14 H14 119.4 . . ? C14 C15 C16 120.29(12) . . ? C14 C15 H15 119.9 . . ? C16 C15 H15 119.9 . . ? O5 C16 C17 124.80(11) . . ? O5 C16 C15 115.51(12) . . ? C17 C16 C15 119.69(11) . . ? C16 C17 C18 119.27(10) . . ? C16 C17 H17 120.4 . . ? C18 C17 H17 120.4 . . ? C17 C18 C13 121.99(11) . . ? C17 C18 H18 119.0 . . ? C13 C18 H18 119.0 . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _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 O2 P1 O3 C10 -3.08(11) . . . . ? O4 P1 O3 C10 -133.57(10) . . . . ? C4 P1 O3 C10 117.28(9) . . . . ? O2 P1 O4 C11 -115.82(13) . . . . ? O3 P1 O4 C11 14.45(14) . . . . ? C4 P1 O4 C11 124.47(12) . . . . ? C8 C1 C2 C3 1.96(17) . . . . ? Cl1 C1 C2 C3 -177.75(8) . . . . ? C1 C2 C3 C6 -0.07(15) . . . . ? C1 C2 C3 C4 -179.39(9) . . . . ? C5 N1 C4 C3 -28.86(13) . . . . ? C5 N1 C4 C9 90.34(11) . . . . ? C5 N1 C4 P1 -148.36(9) . . . . ? C2 C3 C4 N1 -160.15(9) . . . . ? C6 C3 C4 N1 20.52(12) . . . . ? C2 C3 C4 C9 80.97(11) . . . . ? C6 C3 C4 C9 -98.35(10) . . . . ? C2 C3 C4 P1 -43.86(11) . . . . ? C6 C3 C4 P1 136.82(8) . . . . ? O2 P1 C4 N1 81.67(7) . . . . ? O4 P1 C4 N1 -154.11(7) . . . . ? O3 P1 C4 N1 -42.83(7) . . . . ? O2 P1 C4 C3 -37.30(8) . . . . ? O4 P1 C4 C3 86.92(7) . . . . ? O3 P1 C4 C3 -161.80(7) . . . . ? O2 P1 C4 C9 -159.91(7) . . . . ? O4 P1 C4 C9 -35.70(8) . . . . ? O3 P1 C4 C9 75.58(8) . . . . ? C4 N1 C5 O1 -163.15(10) . . . . ? C4 N1 C5 N2 18.60(15) . . . . ? C6 N2 C5 O1 -176.00(10) . . . . ? C12 N2 C5 O1 -1.55(15) . . . . ? C6 N2 C5 N1 2.22(14) . . . . ? C12 N2 C5 N1 176.67(9) . . . . ? C5 N2 C6 C7 170.04(10) . . . . ? C12 N2 C6 C7 -4.12(15) . . . . ? C5 N2 C6 C3 -8.72(14) . . . . ? C12 N2 C6 C3 177.12(9) . . . . ? C2 C3 C6 N2 176.64(9) . . . . ? C4 C3 C6 N2 -4.03(14) . . . . ? C2 C3 C6 C7 -2.15(15) . . . . ? C4 C3 C6 C7 177.18(9) . . . . ? N2 C6 C7 C8 -176.19(10) . . . . ? C3 C6 C7 C8 2.59(17) . . . . ? C2 C1 C8 C7 -1.54(18) . . . . ? Cl1 C1 C8 C7 178.16(9) . . . . ? C6 C7 C8 C1 -0.76(18) . . . . ? N1 C4 C9 F3 -172.80(9) . . . . ? C3 C4 C9 F3 -53.04(12) . . . . ? P1 C4 C9 F3 70.52(11) . . . . ? N1 C4 C9 F2 65.31(11) . . . . ? C3 C4 C9 F2 -174.93(8) . . . . ? P1 C4 C9 F2 -51.37(10) . . . . ? N1 C4 C9 F1 -53.15(11) . . . . ? C3 C4 C9 F1 66.61(11) . . . . ? P1 C4 C9 F1 -169.83(7) . . . . ? C5 N2 C12 C13 96.23(11) . . . . ? C6 N2 C12 C13 -89.29(12) . . . . ? N2 C12 C13 C14 -8.05(16) . . . . ? N2 C12 C13 C18 174.98(10) . . . . ? C18 C13 C14 C15 -0.14(19) . . . . ? C12 C13 C14 C15 -177.15(13) . . . . ? C13 C14 C15 C16 -0.4(2) . . . . ? C19 O5 C16 C17 -3.01(19) . . . . ? C19 O5 C16 C15 176.61(13) . . . . ? C14 C15 C16 O5 -178.87(14) . . . . ? C14 C15 C16 C17 0.8(2) . . . . ? O5 C16 C17 C18 178.94(12) . . . . ? C15 C16 C17 C18 -0.67(18) . . . . ? C16 C17 C18 C13 0.16(17) . . . . ? C14 C13 C18 C17 0.25(17) . . . . ? C12 C13 C18 C17 177.38(10) . . . . ? _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O3 0.87(2) 2.461(19) 2.8587(12) 108.6(15) . N1 H1N O2 0.87(2) 2.01(2) 2.8631(12) 166.2(18) 4_445 C2 H2 O4 0.94 2.55 3.2582(14) 131.9 . C10 H10A O2 0.97 2.55 2.9803(15) 106.9 . C10 H10B O2 0.97 2.51 3.1640(15) 124.3 4_445 C11 H11C O1 0.97 2.34 3.1608(17) 141.5 4_545 C12 H12A O1 0.98 2.30 2.6919(16) 102.5 . C14 H14 F1 0.94 2.51 3.4488(15) 176.4 . C14 H14 N2 0.94 2.53 2.8778(16) 102.2 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 32.88 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.289 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.040