# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Keith Huynh' _publ_contact_author_email Ian.Manners@bristol.ac.uk _publ_section_title ; Donor-Stabilised Cations, Phosphinamide Anions, and Unusual Oxidative Cyclisation Products from Halogenated Phosphoranimines and Phosphinimines with a Bulky 2,4,6-Tri-tert-butylphenyl Substituent at Nitrogen ; loop_ _publ_author_name K.Huynh C.Chun A.Lough I.Manners # Attachment '- 16.cif' data_k05127a _database_code_depnum_ccdc_archive 'CCDC 821782' #TrackingRef '- 16.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H30 F2 N P' _chemical_formula_sum 'C18 H30 F2 N P' _chemical_formula_weight 329.40 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' 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 Orthorhombic _symmetry_space_group_name_H-M 'P n m a' _symmetry_space_group_name_Hall '-P 2ac 2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 19.0219(7) _cell_length_b 15.6776(8) _cell_length_c 6.1422(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1831.71(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 6877 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.166 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f scnas and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 8784 _diffrn_reflns_av_R_equivalents 0.0431 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2133 _reflns_number_gt 1572 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2003)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXTL V6.12 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXTL V6.12 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL V6.12' _computing_publication_material 'SHELXTL V6.12' _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^)+(0.0598P)^2^+0.8536P] 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 ? _refine_ls_extinction_coef none _refine_ls_number_reflns 2133 _refine_ls_number_parameters 125 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.20590(4) 0.2500 0.38405(11) 0.0339(2) Uani 1 2 d S . . F1 F 0.26291(7) 0.17681(7) 0.4252(2) 0.0489(4) Uani 1 1 d . . . N1 N 0.20304(10) 0.2500 0.1176(3) 0.0245(5) Uani 1 2 d S . . H1A H 0.2437 0.2500 0.0492 0.029 Uiso 1 2 calc SR . . C1 C 0.14035(12) 0.2500 -0.0174(4) 0.0229(5) Uani 1 2 d S . . C2 C 0.11120(9) 0.17128(10) -0.0845(3) 0.0227(4) Uani 1 1 d . . . C3 C 0.05027(8) 0.17428(10) -0.2123(3) 0.0247(4) Uani 1 1 d . . . H3A H 0.0296 0.1220 -0.2569 0.030 Uiso 1 1 calc R . . C4 C 0.01862(12) 0.2500 -0.2769(4) 0.0234(5) Uani 1 2 d S . . C5 C 0.14093(9) 0.08217(10) -0.0213(3) 0.0254(4) Uani 1 1 d . . . C6 C 0.12244(10) 0.06227(11) 0.2169(3) 0.0314(4) Uani 1 1 d . . . H6A H 0.1419 0.1067 0.3115 0.047 Uiso 1 1 calc R . . H6B H 0.1424 0.0069 0.2575 0.047 Uiso 1 1 calc R . . H6C H 0.0712 0.0605 0.2337 0.047 Uiso 1 1 calc R . . C7 C 0.22086(9) 0.07489(11) -0.0579(3) 0.0326(4) Uani 1 1 d . . . H7A H 0.2457 0.1058 0.0576 0.049 Uiso 1 1 calc R . . H7B H 0.2330 0.0996 -0.1995 0.049 Uiso 1 1 calc R . . H7C H 0.2347 0.0147 -0.0549 0.049 Uiso 1 1 calc R . . C8 C 0.10776(10) 0.01024(11) -0.1586(3) 0.0349(4) Uani 1 1 d . . . H8A H 0.1298 -0.0443 -0.1209 0.052 Uiso 1 1 calc R . . H8B H 0.1152 0.0221 -0.3136 0.052 Uiso 1 1 calc R . . H8C H 0.0572 0.0072 -0.1286 0.052 Uiso 1 1 calc R . . C9 C -0.04847(12) 0.2500 -0.4139(4) 0.0273(6) Uani 1 2 d S . . C10 C -0.0755(3) 0.3371(3) -0.4712(11) 0.0639(16) Uani 0.50 1 d P A -1 H10A H -0.0852 0.3690 -0.3374 0.096 Uiso 0.50 1 calc PR A -1 H10B H -0.1188 0.3316 -0.5563 0.096 Uiso 0.50 1 calc PR A -1 H10C H -0.0401 0.3675 -0.5572 0.096 Uiso 0.50 1 calc PR A -1 C11 C -0.1055(2) 0.2037(4) -0.2888(11) 0.079(2) Uani 0.50 1 d P A -1 H11A H -0.1158 0.2347 -0.1540 0.118 Uiso 0.50 1 calc PR A -1 H11B H -0.0895 0.1459 -0.2535 0.118 Uiso 0.50 1 calc PR A -1 H11C H -0.1481 0.2005 -0.3781 0.118 Uiso 0.50 1 calc PR A -1 C12 C -0.0344(3) 0.2029(4) -0.6270(9) 0.081(2) Uani 0.50 1 d P A -1 H12A H -0.0772 0.2026 -0.7158 0.121 Uiso 0.50 1 calc PR A -1 H12B H -0.0203 0.1440 -0.5953 0.121 Uiso 0.50 1 calc PR A -1 H12C H 0.0034 0.2317 -0.7066 0.121 Uiso 0.50 1 calc PR A -1 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 0.0400(4) 0.0335(4) 0.0282(4) 0.000 -0.0076(3) 0.000 F1 0.0584(8) 0.0403(7) 0.0481(7) 0.0034(5) -0.0248(6) 0.0084(6) N1 0.0216(10) 0.0249(10) 0.0271(11) 0.000 0.0003(8) 0.000 C1 0.0230(11) 0.0243(11) 0.0214(12) 0.000 -0.0008(9) 0.000 C2 0.0245(8) 0.0205(8) 0.0230(8) 0.0011(6) 0.0028(7) 0.0010(6) C3 0.0260(9) 0.0199(8) 0.0282(9) -0.0005(7) 0.0001(7) -0.0025(6) C4 0.0216(11) 0.0232(11) 0.0253(12) 0.000 0.0002(9) 0.000 C5 0.0290(9) 0.0202(8) 0.0270(9) 0.0017(7) -0.0019(7) 0.0025(6) C6 0.0350(10) 0.0274(9) 0.0319(10) 0.0068(7) 0.0005(8) 0.0002(7) C7 0.0338(10) 0.0251(9) 0.0389(10) 0.0036(8) 0.0042(8) 0.0062(7) C8 0.0443(11) 0.0195(8) 0.0409(11) -0.0006(8) -0.0068(9) 0.0021(7) C9 0.0246(12) 0.0234(12) 0.0339(14) 0.000 -0.0032(10) 0.000 C10 0.050(3) 0.034(2) 0.107(5) 0.012(3) -0.047(3) 0.000(2) C11 0.031(2) 0.107(4) 0.098(4) 0.058(4) -0.021(3) -0.023(3) C12 0.061(3) 0.124(5) 0.057(3) -0.045(3) -0.033(3) 0.039(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F1 1.5990(12) 7_565 ? P1 F1 1.5990(12) . ? P1 N1 1.637(2) . ? N1 C1 1.452(3) . ? C1 C2 1.4143(19) . ? C1 C2 1.4143(19) 7_565 ? C2 C3 1.401(2) . ? C2 C5 1.556(2) . ? C3 C4 1.389(2) . ? C4 C3 1.389(2) 7_565 ? C4 C9 1.529(3) . ? C5 C6 1.537(2) . ? C5 C7 1.541(2) . ? C5 C8 1.543(2) . ? C9 C10 1.501(4) 7_565 ? C9 C10 1.501(4) . ? C9 C11 1.515(5) . ? C9 C11 1.515(5) 7_565 ? C9 C12 1.526(5) . ? C9 C12 1.526(5) 7_565 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 P1 F1 91.72(9) 7_565 . ? F1 P1 N1 100.40(7) 7_565 . ? F1 P1 N1 100.40(7) . . ? C1 N1 P1 126.72(16) . . ? C2 C1 C2 121.5(2) . 7_565 ? C2 C1 N1 119.22(10) . . ? C2 C1 N1 119.22(10) 7_565 . ? C3 C2 C1 117.28(15) . . ? C3 C2 C5 118.07(14) . . ? C1 C2 C5 124.63(15) . . ? C4 C3 C2 123.20(16) . . ? C3 C4 C3 117.5(2) 7_565 . ? C3 C4 C9 121.27(10) 7_565 . ? C3 C4 C9 121.27(10) . . ? C6 C5 C7 110.44(14) . . ? C6 C5 C8 106.17(14) . . ? C7 C5 C8 105.65(14) . . ? C6 C5 C2 109.66(14) . . ? C7 C5 C2 112.87(14) . . ? C8 C5 C2 111.80(14) . . ? C10 C9 C10 131.0(4) 7_565 . ? C10 C9 C11 55.8(4) 7_565 . ? C10 C9 C11 108.0(4) . . ? C10 C9 C11 108.0(4) 7_565 7_565 ? C10 C9 C11 55.8(4) . 7_565 ? C11 C9 C11 57.3(6) . 7_565 ? C10 C9 C12 54.5(3) 7_565 . ? C10 C9 C12 107.4(4) . . ? C11 C9 C12 109.2(4) . . ? C11 C9 C12 142.4(3) 7_565 . ? C10 C9 C12 107.4(4) 7_565 7_565 ? C10 C9 C12 54.5(3) . 7_565 ? C11 C9 C12 142.4(3) . 7_565 ? C11 C9 C12 109.2(4) 7_565 7_565 ? C12 C9 C12 57.9(6) . 7_565 ? C10 C9 C4 114.50(19) 7_565 . ? C10 C9 C4 114.50(19) . . ? C11 C9 C4 108.6(2) . . ? C11 C9 C4 108.6(2) 7_565 . ? C12 C9 C4 109.0(2) . . ? C12 C9 C4 109.0(2) 7_565 . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.289 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.052 # Attachment '- 18.cif' data_k0638 _database_code_depnum_ccdc_archive 'CCDC 821783' #TrackingRef '- 18.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H29 Cl N O2 P' _chemical_formula_sum 'C18 H29 Cl N O2 P' _chemical_formula_weight 357.84 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1257(3) _cell_length_b 13.9396(7) _cell_length_c 15.6039(6) _cell_angle_alpha 90.00 _cell_angle_beta 95.608(3) _cell_angle_gamma 90.00 _cell_volume 1975.45(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 13533 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.283 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.808 _exptl_absorpt_correction_T_max 0.958 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13533 _diffrn_reflns_av_R_equivalents 0.0802 _diffrn_reflns_av_sigmaI/netI 0.0830 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.68 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4506 _reflns_number_gt 2824 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2003)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXTL V6.1(Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL V6.1(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.1' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0759P)^2^+0.4857P] 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 4506 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0575 _refine_ls_wR_factor_ref 0.1615 _refine_ls_wR_factor_gt 0.1372 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 Cl1 Cl 0.43572(8) 0.38133(5) 0.22006(5) 0.0506(2) Uani 1 1 d . . . P1 P 0.39873(7) 0.25080(5) 0.26768(4) 0.0360(2) Uani 1 1 d . . . O1 O 0.42910(17) 0.17948(13) 0.19212(10) 0.0326(4) Uani 1 1 d . . . O2 O 0.25300(18) 0.24686(15) 0.29960(12) 0.0406(5) Uani 1 1 d . . . N1 N 0.5505(2) 0.23188(16) 0.33441(13) 0.0351(5) Uani 1 1 d . . . C1 C 0.5678(2) 0.12680(18) 0.21332(15) 0.0286(6) Uani 1 1 d . . . C2 C 0.6675(3) 0.14191(18) 0.14421(15) 0.0300(6) Uani 1 1 d . . . H2A H 0.6279 0.1446 0.0856 0.036 Uiso 1 1 calc R . . C3 C 0.8134(3) 0.15175(18) 0.16478(15) 0.0284(5) Uani 1 1 d . . . C4 C 0.8725(3) 0.15073(18) 0.25629(15) 0.0291(5) Uani 1 1 d . . . H4A H 0.9762 0.1452 0.2688 0.035 Uiso 1 1 calc R . . C5 C 0.7909(2) 0.15704(18) 0.32341(15) 0.0281(5) Uani 1 1 d . . . C6 C 0.6327(3) 0.17310(18) 0.29671(15) 0.0283(5) Uani 1 1 d . . . C7 C 0.5226(3) 0.01828(19) 0.22339(17) 0.0358(6) Uani 1 1 d . . . C8 C 0.4396(3) -0.0147(2) 0.13852(19) 0.0465(7) Uani 1 1 d . . . H8A H 0.4018 -0.0798 0.1454 0.070 Uiso 1 1 calc R . . H8B H 0.5065 -0.0145 0.0931 0.070 Uiso 1 1 calc R . . H8C H 0.3572 0.0289 0.1228 0.070 Uiso 1 1 calc R . . C9 C 0.6589(3) -0.0457(2) 0.24333(19) 0.0399(6) Uani 1 1 d . . . H9A H 0.6282 -0.1130 0.2451 0.060 Uiso 1 1 calc R . . H9B H 0.7096 -0.0276 0.2992 0.060 Uiso 1 1 calc R . . H9C H 0.7257 -0.0373 0.1984 0.060 Uiso 1 1 calc R . . C10 C 0.4216(3) 0.0078(2) 0.29612(19) 0.0463(7) Uani 1 1 d . . . H10A H 0.3884 -0.0589 0.2989 0.069 Uiso 1 1 calc R . . H10B H 0.3360 0.0500 0.2847 0.069 Uiso 1 1 calc R . . H10C H 0.4760 0.0255 0.3511 0.069 Uiso 1 1 calc R . . C11 C 0.9226(3) 0.16178(19) 0.09703(16) 0.0333(6) Uani 1 1 d . . . C12 C 1.0018(3) 0.2581(2) 0.11090(19) 0.0487(8) Uani 1 1 d . . . H12A H 0.9310 0.3105 0.0992 0.073 Uiso 1 1 calc R . . H12B H 1.0792 0.2631 0.0718 0.073 Uiso 1 1 calc R . . H12C H 1.0459 0.2625 0.1706 0.073 Uiso 1 1 calc R . . C13 C 1.0363(3) 0.0805(2) 0.10794(18) 0.0470(7) Uani 1 1 d . . . H13A H 0.9858 0.0185 0.1011 0.070 Uiso 1 1 calc R . . H13B H 1.0899 0.0842 0.1654 0.070 Uiso 1 1 calc R . . H13C H 1.1059 0.0868 0.0642 0.070 Uiso 1 1 calc R . . C14 C 0.8476(3) 0.1574(2) 0.00569(16) 0.0448(7) Uani 1 1 d . . . H14A H 0.7748 0.2091 -0.0027 0.067 Uiso 1 1 calc R . . H14B H 0.7983 0.0953 -0.0037 0.067 Uiso 1 1 calc R . . H14C H 0.9214 0.1651 -0.0354 0.067 Uiso 1 1 calc R . . C15 C 0.8500(3) 0.15925(19) 0.41793(15) 0.0318(6) Uani 1 1 d . . . C16 C 1.0095(3) 0.1221(2) 0.43032(17) 0.0432(7) Uani 1 1 d . . . H16A H 1.0139 0.0577 0.4057 0.065 Uiso 1 1 calc R . . H16B H 1.0428 0.1198 0.4919 0.065 Uiso 1 1 calc R . . H16C H 1.0734 0.1654 0.4013 0.065 Uiso 1 1 calc R . . C17 C 0.7554(3) 0.0945(2) 0.47012(16) 0.0395(7) Uani 1 1 d . . . H17A H 0.6531 0.1169 0.4632 0.059 Uiso 1 1 calc R . . H17B H 0.7929 0.0971 0.5311 0.059 Uiso 1 1 calc R . . H17C H 0.7600 0.0284 0.4494 0.059 Uiso 1 1 calc R . . C18 C 0.8482(3) 0.2627(2) 0.45302(17) 0.0414(7) Uani 1 1 d . . . H18A H 0.7476 0.2880 0.4449 0.062 Uiso 1 1 calc R . . H18B H 0.9131 0.3031 0.4219 0.062 Uiso 1 1 calc R . . H18C H 0.8826 0.2626 0.5145 0.062 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 Cl1 0.0475(4) 0.0420(4) 0.0603(5) -0.0007(4) -0.0041(4) 0.0085(3) P1 0.0271(4) 0.0473(5) 0.0331(4) -0.0071(3) 0.0006(3) 0.0070(3) O1 0.0252(8) 0.0421(11) 0.0294(9) -0.0058(8) -0.0024(7) 0.0079(7) O2 0.0206(9) 0.0656(14) 0.0366(10) -0.0083(9) 0.0073(7) 0.0053(8) N1 0.0284(11) 0.0469(14) 0.0305(11) -0.0059(10) 0.0046(9) 0.0049(10) C1 0.0204(11) 0.0373(15) 0.0276(12) -0.0010(11) 0.0004(10) 0.0040(10) C2 0.0310(13) 0.0356(14) 0.0232(12) -0.0002(11) 0.0015(10) 0.0051(11) C3 0.0280(12) 0.0310(13) 0.0265(12) 0.0003(11) 0.0032(10) 0.0033(10) C4 0.0238(12) 0.0349(14) 0.0285(12) 0.0000(11) 0.0014(10) 0.0018(10) C5 0.0251(12) 0.0311(13) 0.0279(12) -0.0007(11) 0.0013(10) -0.0008(10) C6 0.0259(12) 0.0332(14) 0.0258(12) 0.0029(11) 0.0029(10) -0.0003(10) C7 0.0297(13) 0.0369(15) 0.0406(15) -0.0047(12) 0.0021(11) -0.0019(11) C8 0.0373(15) 0.0437(17) 0.0565(19) -0.0145(15) -0.0056(14) 0.0001(13) C9 0.0355(14) 0.0344(15) 0.0495(16) 0.0026(13) 0.0019(12) 0.0019(12) C10 0.0379(15) 0.0448(18) 0.0583(19) 0.0008(15) 0.0153(14) -0.0072(13) C11 0.0315(13) 0.0392(15) 0.0301(13) 0.0019(12) 0.0071(11) 0.0030(11) C12 0.0514(18) 0.0560(19) 0.0411(16) 0.0021(15) 0.0168(14) -0.0076(15) C13 0.0377(15) 0.067(2) 0.0370(15) 0.0021(15) 0.0101(12) 0.0156(14) C14 0.0405(15) 0.067(2) 0.0282(13) 0.0026(14) 0.0086(12) 0.0069(14) C15 0.0264(12) 0.0418(15) 0.0270(12) 0.0015(12) 0.0018(10) -0.0003(11) C16 0.0331(14) 0.069(2) 0.0267(13) 0.0044(13) -0.0023(11) 0.0037(14) C17 0.0368(14) 0.0520(17) 0.0297(13) 0.0067(13) 0.0027(11) 0.0011(13) C18 0.0457(16) 0.0486(17) 0.0288(13) -0.0031(13) -0.0011(12) -0.0071(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 Cl1 P1 2.0064(11) . ? P1 O2 1.4660(18) . ? P1 O1 1.5872(17) . ? P1 N1 1.670(2) . ? O1 C1 1.473(3) . ? N1 C6 1.291(3) . ? C1 C2 1.492(3) . ? C1 C6 1.520(3) . ? C1 C7 1.580(4) . ? C2 C3 1.346(3) . ? C3 C4 1.477(3) . ? C3 C11 1.528(3) . ? C4 C5 1.346(3) . ? C5 C6 1.480(3) . ? C5 C15 1.520(3) . ? C7 C8 1.531(4) . ? C7 C9 1.537(4) . ? C7 C10 1.538(4) . ? C11 C14 1.521(3) . ? C11 C12 1.530(4) . ? C11 C13 1.535(4) . ? C15 C17 1.536(4) . ? C15 C16 1.539(3) . ? C15 C18 1.543(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 O2 P1 O1 117.32(11) . . ? O2 P1 N1 120.44(11) . . ? O1 P1 N1 99.78(10) . . ? O2 P1 Cl1 110.54(9) . . ? O1 P1 Cl1 104.18(8) . . ? N1 P1 Cl1 102.41(9) . . ? C1 O1 P1 110.74(14) . . ? C6 N1 P1 107.43(17) . . ? O1 C1 C2 109.79(19) . . ? O1 C1 C6 103.59(18) . . ? C2 C1 C6 110.16(19) . . ? O1 C1 C7 105.86(18) . . ? C2 C1 C7 113.0(2) . . ? C6 C1 C7 113.9(2) . . ? C3 C2 C1 120.1(2) . . ? C2 C3 C4 119.3(2) . . ? C2 C3 C11 122.8(2) . . ? C4 C3 C11 117.9(2) . . ? C5 C4 C3 125.0(2) . . ? C4 C5 C6 112.9(2) . . ? C4 C5 C15 125.8(2) . . ? C6 C5 C15 120.9(2) . . ? N1 C6 C5 124.2(2) . . ? N1 C6 C1 117.7(2) . . ? C5 C6 C1 117.7(2) . . ? C8 C7 C9 108.8(2) . . ? C8 C7 C10 109.1(2) . . ? C9 C7 C10 109.1(2) . . ? C8 C7 C1 108.3(2) . . ? C9 C7 C1 111.2(2) . . ? C10 C7 C1 110.2(2) . . ? C14 C11 C3 112.4(2) . . ? C14 C11 C12 109.3(2) . . ? C3 C11 C12 108.3(2) . . ? C14 C11 C13 108.2(2) . . ? C3 C11 C13 109.6(2) . . ? C12 C11 C13 109.1(2) . . ? C5 C15 C17 109.8(2) . . ? C5 C15 C16 110.9(2) . . ? C17 C15 C16 108.0(2) . . ? C5 C15 C18 110.4(2) . . ? C17 C15 C18 109.5(2) . . ? C16 C15 C18 108.2(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.433 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.091 # Attachment '- [9]OTf.cif' data_k0472 _database_code_depnum_ccdc_archive 'CCDC 821784' #TrackingRef '- [9]OTf.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H39 Cl2 N3 P, C F3 O3 S, C H2 Cl2' _chemical_formula_sum 'C27 H41 Cl4 F3 N3 O3 P S' _chemical_formula_weight 717.46 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7008(2) _cell_length_b 10.6081(3) _cell_length_c 20.7723(6) _cell_angle_alpha 98.8000(16) _cell_angle_beta 90.9900(18) _cell_angle_gamma 112.4650(15) _cell_volume 1744.88(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 19547 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 27.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.366 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 0.493 # Absorption correction _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.703 _exptl_absorpt_correction_T_max 0.970 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19547 _diffrn_reflns_av_R_equivalents 0.0628 _diffrn_reflns_av_sigmaI/netI 0.0633 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7963 _reflns_number_gt 5618 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius B.V., 1997-2002)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction Denzo-SMN _computing_structure_solution 'SHELXTL V6.1(Sheldrick, 2001)' _computing_structure_refinement 'SHELXTL V6.1(Sheldrick, 2001)' _computing_molecular_graphics 'SHELXTL V6.1' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0583P)^2^+1.0015P] 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 SHELXL _refine_ls_extinction_coef 0.0044(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7963 _refine_ls_number_parameters 391 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0808 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1391 _refine_ls_wR_factor_gt 0.1194 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Cl1 Cl 0.25824(9) 0.48298(6) 0.22248(3) 0.04042(18) Uani 1 1 d . . . Cl2 Cl 0.02224(7) 0.63639(7) 0.24835(3) 0.03867(18) Uani 1 1 d . . . P1 P 0.26560(7) 0.67646(6) 0.24228(3) 0.02605(16) Uani 1 1 d . . . N1 N 0.3401(2) 0.7204(2) 0.32352(10) 0.0263(4) Uani 1 1 d . . . N2 N 0.5572(2) 0.8066(2) 0.51189(10) 0.0290(4) Uani 1 1 d . . . N3 N 0.3566(2) 0.7790(2) 0.20206(10) 0.0272(4) Uani 1 1 d . . . C1 C 0.2639(3) 0.6400(3) 0.36935(13) 0.0306(5) Uani 1 1 d . . . H1A H 0.1622 0.5621 0.3565 0.037 Uiso 1 1 calc R . . C2 C 0.3291(3) 0.6684(3) 0.43121(13) 0.0312(5) Uani 1 1 d . . . H2A H 0.2724 0.6112 0.4614 0.037 Uiso 1 1 calc R . . C3 C 0.4836(3) 0.7845(2) 0.45273(12) 0.0257(5) Uani 1 1 d . . . C4 C 0.5541(3) 0.8711(2) 0.40549(12) 0.0280(5) Uani 1 1 d . . . H4A H 0.6506 0.9538 0.4180 0.034 Uiso 1 1 calc R . . C5 C 0.4846(3) 0.8362(2) 0.34337(12) 0.0265(5) Uani 1 1 d . . . H5A H 0.5367 0.8931 0.3124 0.032 Uiso 1 1 calc R . . C6 C 0.4919(3) 0.7079(3) 0.55713(13) 0.0364(6) Uani 1 1 d . . . H6A H 0.4585 0.6132 0.5332 0.055 Uiso 1 1 calc R . . H6B H 0.3949 0.7193 0.5763 0.055 Uiso 1 1 calc R . . H6C H 0.5787 0.7256 0.5920 0.055 Uiso 1 1 calc R . . C7 C 0.7111(3) 0.9278(3) 0.53598(13) 0.0336(6) Uani 1 1 d . . . H7A H 0.7004 1.0113 0.5256 0.050 Uiso 0.50 1 calc PR . . H7B H 0.8057 0.9159 0.5150 0.050 Uiso 0.50 1 calc PR . . H7C H 0.7296 0.9370 0.5834 0.050 Uiso 0.50 1 calc PR . . H7D H 0.7901 0.8982 0.5571 0.050 Uiso 0.50 1 calc PR . . H7E H 0.6848 0.9936 0.5677 0.050 Uiso 0.50 1 calc PR . . H7F H 0.7609 0.9725 0.4992 0.050 Uiso 0.50 1 calc PR . . C8 C 0.4624(3) 0.8798(2) 0.16785(11) 0.0237(5) Uani 1 1 d . . . C9 C 0.4476(3) 1.0088(2) 0.17289(11) 0.0256(5) Uani 1 1 d . . . C10 C 0.5619(3) 1.1094(2) 0.14217(12) 0.0289(5) Uani 1 1 d . . . H10A H 0.5554 1.1976 0.1465 0.035 Uiso 1 1 calc R . . C11 C 0.6842(3) 1.0873(2) 0.10576(11) 0.0277(5) Uani 1 1 d . . . C12 C 0.6896(3) 0.9572(2) 0.09980(11) 0.0275(5) Uani 1 1 d . . . H12A H 0.7710 0.9394 0.0743 0.033 Uiso 1 1 calc R . . C13 C 0.5819(3) 0.8508(2) 0.12928(11) 0.0250(5) Uani 1 1 d . . . C14 C 0.3080(3) 1.0429(3) 0.20707(13) 0.0305(5) Uani 1 1 d . . . C15 C 0.3083(3) 1.0327(3) 0.28015(13) 0.0353(6) Uani 1 1 d . . . H15A H 0.4206 1.0870 0.3016 0.053 Uiso 1 1 calc R . . H15B H 0.2752 0.9356 0.2850 0.053 Uiso 1 1 calc R . . H15C H 0.2292 1.0689 0.3004 0.053 Uiso 1 1 calc R . . C16 C 0.1374(3) 0.9459(3) 0.17135(14) 0.0379(6) Uani 1 1 d . . . H16A H 0.1232 0.8493 0.1703 0.057 Uiso 1 1 calc R . . H16B H 0.1323 0.9633 0.1265 0.057 Uiso 1 1 calc R . . H16C H 0.0483 0.9632 0.1945 0.057 Uiso 1 1 calc R . . C17 C 0.3245(4) 1.1919(3) 0.20434(17) 0.0459(7) Uani 1 1 d . . . H17A H 0.4303 1.2578 0.2277 0.069 Uiso 1 1 calc R . . H17B H 0.2316 1.2079 0.2249 0.069 Uiso 1 1 calc R . . H17C H 0.3221 1.2047 0.1587 0.069 Uiso 1 1 calc R . . C18 C 0.8041(3) 1.1976(3) 0.07068(12) 0.0328(6) Uani 1 1 d . . . C19 C 0.8041(5) 1.3408(4) 0.0939(2) 0.0788(13) Uani 1 1 d . . . H19A H 0.8316 1.3664 0.1413 0.118 Uiso 1 1 calc R . . H19B H 0.6933 1.3398 0.0833 0.118 Uiso 1 1 calc R . . H19C H 0.8873 1.4084 0.0720 0.118 Uiso 1 1 calc R . . C20 C 0.7543(5) 1.1567(4) -0.00224(16) 0.0790(14) Uani 1 1 d . . . H20A H 0.6431 1.1563 -0.0110 0.119 Uiso 1 1 calc R . . H20B H 0.7526 1.0640 -0.0175 0.119 Uiso 1 1 calc R . . H20C H 0.8352 1.2234 -0.0253 0.119 Uiso 1 1 calc R . . C21 C 0.9825(4) 1.2082(4) 0.0828(2) 0.0677(11) Uani 1 1 d . . . H21A H 1.0114 1.2234 0.1300 0.102 Uiso 1 1 calc R . . H21B H 1.0595 1.2858 0.0643 0.102 Uiso 1 1 calc R . . H21C H 0.9911 1.1220 0.0621 0.102 Uiso 1 1 calc R . . C22 C 0.5964(3) 0.7085(3) 0.11823(12) 0.0304(5) Uani 1 1 d . . . C23 C 0.7285(4) 0.7035(3) 0.07047(15) 0.0426(7) Uani 1 1 d . . . H23A H 0.8378 0.7743 0.0882 0.064 Uiso 1 1 calc R . . H23B H 0.6980 0.7212 0.0281 0.064 Uiso 1 1 calc R . . H23C H 0.7338 0.6119 0.0648 0.064 Uiso 1 1 calc R . . C24 C 0.6539(3) 0.6800(3) 0.18281(13) 0.0348(6) Uani 1 1 d . . . H24A H 0.5769 0.6863 0.2158 0.052 Uiso 1 1 calc R . . H24B H 0.7664 0.7486 0.1978 0.052 Uiso 1 1 calc R . . H24C H 0.6552 0.5869 0.1760 0.052 Uiso 1 1 calc R . . C25 C 0.4303(3) 0.5947(3) 0.08597(13) 0.0360(6) Uani 1 1 d . . . H25A H 0.3376 0.6034 0.1098 0.054 Uiso 1 1 calc R . . H25B H 0.4326 0.5034 0.0871 0.054 Uiso 1 1 calc R . . H25C H 0.4151 0.6049 0.0405 0.054 Uiso 1 1 calc R . . Cl3 Cl 0.93039(10) 0.81650(8) 0.39254(4) 0.0564(2) Uani 1 1 d . . . Cl4 Cl 0.65055(10) 0.55466(8) 0.34775(4) 0.0543(2) Uani 1 1 d . . . C27 C 0.8160(4) 0.6489(3) 0.40842(16) 0.0473(7) Uani 1 1 d . . . H27A H 0.7704 0.6558 0.4516 0.057 Uiso 1 1 calc R . . H27B H 0.8912 0.5990 0.4101 0.057 Uiso 1 1 calc R . . S1 S -0.03814(8) 0.28027(7) 0.41322(4) 0.03879(19) Uani 1 1 d . . . F1 F -0.0126(3) 0.2621(2) 0.28706(11) 0.0855(7) Uani 1 1 d . . . F2 F -0.0898(4) 0.0674(2) 0.32059(13) 0.0950(8) Uani 1 1 d . . . F3 F -0.2620(2) 0.1641(3) 0.31432(10) 0.0777(7) Uani 1 1 d . . . O1 O 0.1312(3) 0.2955(3) 0.42242(16) 0.0763(8) Uani 1 1 d . . . O2 O -0.0584(3) 0.4074(2) 0.41236(12) 0.0506(5) Uani 1 1 d . . . O3 O -0.1553(3) 0.1884(2) 0.45018(11) 0.0550(6) Uani 1 1 d . . . C26 C -0.1041(4) 0.1904(3) 0.32947(17) 0.0512(8) 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 Cl1 0.0539(4) 0.0211(3) 0.0451(4) 0.0076(3) 0.0123(3) 0.0123(3) Cl2 0.0264(3) 0.0431(4) 0.0434(4) 0.0119(3) 0.0025(3) 0.0086(3) P1 0.0268(3) 0.0218(3) 0.0285(3) 0.0059(2) 0.0030(2) 0.0078(2) N1 0.0258(10) 0.0231(10) 0.0288(10) 0.0097(8) 0.0034(8) 0.0062(8) N2 0.0276(10) 0.0303(11) 0.0297(11) 0.0117(9) 0.0060(8) 0.0092(9) N3 0.0314(10) 0.0239(10) 0.0287(11) 0.0083(8) 0.0062(8) 0.0120(9) C1 0.0261(12) 0.0259(12) 0.0376(14) 0.0127(10) 0.0061(10) 0.0047(10) C2 0.0280(12) 0.0295(13) 0.0349(14) 0.0153(11) 0.0083(10) 0.0061(10) C3 0.0274(11) 0.0244(12) 0.0286(12) 0.0081(9) 0.0064(10) 0.0122(10) C4 0.0279(12) 0.0226(12) 0.0330(13) 0.0075(10) 0.0037(10) 0.0084(10) C5 0.0269(11) 0.0210(11) 0.0314(13) 0.0107(9) 0.0053(10) 0.0065(9) C6 0.0369(14) 0.0397(15) 0.0330(14) 0.0174(12) 0.0064(11) 0.0111(12) C7 0.0348(13) 0.0299(13) 0.0327(14) 0.0069(11) 0.0014(11) 0.0082(11) C8 0.0258(11) 0.0229(11) 0.0212(11) 0.0047(9) -0.0006(9) 0.0080(9) C9 0.0301(12) 0.0244(12) 0.0240(11) 0.0031(9) 0.0001(9) 0.0130(10) C10 0.0345(13) 0.0223(12) 0.0298(13) 0.0057(10) -0.0010(10) 0.0107(10) C11 0.0286(12) 0.0283(13) 0.0240(12) 0.0060(10) 0.0000(9) 0.0084(10) C12 0.0301(12) 0.0283(13) 0.0231(12) 0.0045(10) 0.0042(9) 0.0104(10) C13 0.0293(12) 0.0259(12) 0.0205(11) 0.0028(9) -0.0004(9) 0.0122(10) C14 0.0335(13) 0.0260(13) 0.0373(14) 0.0080(10) 0.0068(11) 0.0164(11) C15 0.0404(14) 0.0348(14) 0.0349(14) 0.0020(11) 0.0069(11) 0.0208(12) C16 0.0348(14) 0.0399(15) 0.0441(16) 0.0107(12) 0.0034(12) 0.0188(12) C17 0.0502(17) 0.0362(16) 0.065(2) 0.0173(14) 0.0178(15) 0.0280(14) C18 0.0368(13) 0.0296(13) 0.0301(13) 0.0108(10) 0.0024(11) 0.0089(11) C19 0.097(3) 0.0328(18) 0.104(3) 0.0249(19) 0.054(3) 0.0152(19) C20 0.087(3) 0.075(3) 0.0382(18) 0.0296(18) -0.0079(18) -0.016(2) C21 0.0408(17) 0.060(2) 0.102(3) 0.045(2) 0.0161(18) 0.0078(16) C22 0.0336(13) 0.0272(13) 0.0321(13) 0.0026(10) 0.0054(10) 0.0147(11) C23 0.0489(16) 0.0334(15) 0.0480(17) 0.0026(13) 0.0169(13) 0.0198(13) C24 0.0350(13) 0.0303(13) 0.0429(15) 0.0078(11) 0.0019(11) 0.0165(11) C25 0.0442(15) 0.0258(13) 0.0332(14) 0.0000(11) 0.0013(11) 0.0103(11) Cl3 0.0485(4) 0.0439(4) 0.0705(6) 0.0058(4) 0.0063(4) 0.0126(3) Cl4 0.0502(4) 0.0419(4) 0.0677(5) 0.0170(4) 0.0032(4) 0.0118(3) C27 0.0549(18) 0.0450(17) 0.0515(18) 0.0155(14) 0.0067(14) 0.0271(15) S1 0.0305(3) 0.0289(3) 0.0593(5) 0.0194(3) 0.0049(3) 0.0096(3) F1 0.0895(16) 0.0799(16) 0.0701(15) 0.0297(12) 0.0441(12) 0.0065(13) F2 0.124(2) 0.0482(13) 0.111(2) 0.0030(13) 0.0502(17) 0.0333(14) F3 0.0491(11) 0.1003(18) 0.0603(13) 0.0038(12) -0.0032(10) 0.0077(11) O1 0.0410(13) 0.0784(18) 0.120(2) 0.0323(17) -0.0023(14) 0.0298(13) O2 0.0464(11) 0.0291(11) 0.0782(16) 0.0166(10) 0.0093(11) 0.0139(9) O3 0.0664(14) 0.0361(12) 0.0516(13) 0.0201(10) 0.0125(11) 0.0029(10) C26 0.0492(18) 0.0423(18) 0.059(2) 0.0170(15) 0.0242(15) 0.0107(14) _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 Cl1 P1 2.0065(9) . ? Cl2 P1 2.0044(9) . ? P1 N3 1.467(2) . ? P1 N1 1.725(2) . ? N1 C5 1.381(3) . ? N1 C1 1.383(3) . ? N2 C3 1.321(3) . ? N2 C7 1.470(3) . ? N2 C6 1.472(3) . ? N3 C8 1.414(3) . ? C1 C2 1.337(4) . ? C2 C3 1.439(3) . ? C3 C4 1.431(3) . ? C4 C5 1.350(3) . ? C8 C9 1.410(3) . ? C8 C13 1.420(3) . ? C9 C10 1.398(3) . ? C9 C14 1.548(3) . ? C10 C11 1.387(4) . ? C11 C12 1.385(3) . ? C11 C18 1.531(3) . ? C12 C13 1.396(3) . ? C13 C22 1.545(3) . ? C14 C15 1.538(4) . ? C14 C16 1.541(4) . ? C14 C17 1.541(3) . ? C18 C20 1.518(4) . ? C18 C19 1.521(4) . ? C18 C21 1.527(4) . ? C22 C24 1.536(4) . ? C22 C23 1.542(4) . ? C22 C25 1.543(3) . ? Cl3 C27 1.760(3) . ? Cl4 C27 1.764(3) . ? S1 O1 1.426(2) . ? S1 O2 1.428(2) . ? S1 O3 1.440(2) . ? S1 C26 1.818(4) . ? F1 C26 1.325(4) . ? F2 C26 1.342(4) . ? F3 C26 1.315(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 N3 P1 N1 114.16(11) . . ? N3 P1 Cl2 117.20(8) . . ? N1 P1 Cl2 101.94(7) . . ? N3 P1 Cl1 120.21(9) . . ? N1 P1 Cl1 100.08(7) . . ? Cl2 P1 Cl1 100.27(4) . . ? C5 N1 C1 118.4(2) . . ? C5 N1 P1 119.34(16) . . ? C1 N1 P1 122.16(17) . . ? C3 N2 C7 122.6(2) . . ? C3 N2 C6 121.5(2) . . ? C7 N2 C6 115.9(2) . . ? C8 N3 P1 172.95(18) . . ? C2 C1 N1 122.0(2) . . ? C1 C2 C3 121.0(2) . . ? N2 C3 C4 122.5(2) . . ? N2 C3 C2 121.6(2) . . ? C4 C3 C2 115.8(2) . . ? C5 C4 C3 120.6(2) . . ? C4 C5 N1 122.0(2) . . ? C9 C8 N3 119.1(2) . . ? C9 C8 C13 120.9(2) . . ? N3 C8 C13 120.0(2) . . ? C10 C9 C8 117.5(2) . . ? C10 C9 C14 118.2(2) . . ? C8 C9 C14 124.2(2) . . ? C11 C10 C9 123.5(2) . . ? C12 C11 C10 117.0(2) . . ? C12 C11 C18 120.5(2) . . ? C10 C11 C18 122.5(2) . . ? C11 C12 C13 123.5(2) . . ? C12 C13 C8 117.4(2) . . ? C12 C13 C22 119.3(2) . . ? C8 C13 C22 123.3(2) . . ? C15 C14 C16 110.1(2) . . ? C15 C14 C17 105.3(2) . . ? C16 C14 C17 106.5(2) . . ? C15 C14 C9 113.36(19) . . ? C16 C14 C9 109.2(2) . . ? C17 C14 C9 112.2(2) . . ? C20 C18 C19 109.0(3) . . ? C20 C18 C21 108.7(3) . . ? C19 C18 C21 107.3(3) . . ? C20 C18 C11 109.0(2) . . ? C19 C18 C11 112.6(2) . . ? C21 C18 C11 110.2(2) . . ? C24 C22 C23 105.9(2) . . ? C24 C22 C25 113.3(2) . . ? C23 C22 C25 105.4(2) . . ? C24 C22 C13 110.0(2) . . ? C23 C22 C13 112.0(2) . . ? C25 C22 C13 110.06(19) . . ? Cl3 C27 Cl4 111.37(16) . . ? O1 S1 O2 114.12(15) . . ? O1 S1 O3 116.22(16) . . ? O2 S1 O3 114.35(14) . . ? O1 S1 C26 104.33(17) . . ? O2 S1 C26 102.73(15) . . ? O3 S1 C26 102.73(14) . . ? F3 C26 F1 108.8(3) . . ? F3 C26 F2 106.3(3) . . ? F1 C26 F2 107.0(3) . . ? F3 C26 S1 111.5(2) . . ? F1 C26 S1 111.8(2) . . ? F2 C26 S1 111.2(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.490 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.069