Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2002 data_mh1012e _database_code_CSD 193475 _journal_coden_Cambridge 186 loop_ _publ_author_name 'Phil Dyer' 'John Fawcett' 'Martin J.Hanton' 'R.Kemmitt' 'Ranbir Padda' 'Narendra Singh' _publ_contact_author_name 'Dr Phil Dyer' _publ_contact_author_address ; Department of Chemistry University of Leicester University Road Leicester LE17RH UNITED KINGDOM ; _publ_contact_author_email 'P.DYER@LE.AC.UK' _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Exploring the coordination chemistry and reactivity of dialkylamino- and bis-(dialkylamino)-phosphines in the coordination sphere of metals ; _audit_creation_method SHELXL-97 _chemical_name_systematic 'bis(Diisopropylamino) pentafluorophenyl phosphine' _chemical_name_common 'bis(Diisopropylamino) perfluorophenyl phosphine' _chemical_melting_point ? _chemical_formula_moiety 'C18 H28 F5 N2 P' _chemical_formula_sum 'C18 H28 F5 N2 P' _chemical_formula_weight 398.39 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 Pbca loop_ _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' '-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 12.9383(15) _cell_length_b 10.3076(19) _cell_length_c 29.874(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3984.1(10) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 12122 _cell_measurement_theta_min 2.621 _cell_measurement_theta_max 26.997 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.782 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; 1739 reflections corrected using SADABS. R(int) = 0.0223 before correction. R(int) = 0.0149 after correction. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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_% <1 _diffrn_reflns_number 1688 _diffrn_reflns_av_R_equivalents 0.0336 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 26.31 _reflns_number_total 1092 _reflns_number_gt 783 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.0278P)^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 1092 _refine_ls_number_parameters 243 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0316 _refine_ls_wR_factor_ref 0.0668 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_restrained_S_all 0.899 _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 0.92016(8) 0.15869(12) 0.37877(4) 0.0265(4) Uani 1 1 d . . . F1 F 0.91186(17) -0.0904(2) 0.42546(8) 0.0409(8) Uani 1 1 d . . . F2 F 1.01806(19) -0.3109(3) 0.41755(10) 0.0510(8) Uani 1 1 d . . . F3 F 1.1764(2) -0.3294(3) 0.35811(9) 0.0523(9) Uani 1 1 d . . . F4 F 1.22469(17) -0.1217(3) 0.30582(9) 0.0491(8) Uani 1 1 d . . . F5 F 1.11937(16) 0.0988(3) 0.31226(10) 0.0414(8) Uani 1 1 d . . . N1 N 0.9908(2) 0.2361(3) 0.41782(11) 0.0247(10) Uani 1 1 d . . . N2 N 0.9182(2) 0.2473(3) 0.33204(12) 0.0262(10) Uani 1 1 d . . . C1 C 1.0091(3) 0.0152(5) 0.36906(16) 0.0272(12) Uani 1 1 d . . . C2 C 0.9884(3) -0.0936(5) 0.39474(16) 0.0304(12) Uani 1 1 d . . . C3 C 1.0421(3) -0.2084(5) 0.39145(18) 0.0344(14) Uani 1 1 d . . . C4 C 1.1222(3) -0.2182(5) 0.36122(19) 0.0378(16) Uani 1 1 d . . . C5 C 1.1465(3) -0.1134(5) 0.33529(18) 0.0346(14) Uani 1 1 d . . . C6 C 1.0895(3) -0.0008(5) 0.33885(17) 0.0295(12) Uani 1 1 d . . . C7 C 1.1445(3) 0.3830(4) 0.42399(17) 0.0388(14) Uani 1 1 d . . . H7A H 1.1150 0.4377 0.4004 0.058 Uiso 1 1 calc R . . H7B H 1.2200 0.3837 0.4216 0.058 Uiso 1 1 calc R . . H7C H 1.1238 0.4168 0.4533 0.058 Uiso 1 1 calc R . . C8 C 1.1048(3) 0.2439(4) 0.41870(17) 0.0295(13) Uani 1 1 d . . . H8 H 1.1302 0.2115 0.3891 0.035 Uiso 1 1 calc R . . C9 C 1.1522(3) 0.1557(5) 0.45502(16) 0.0392(14) Uani 1 1 d . . . H9A H 1.1370 0.1916 0.4847 0.059 Uiso 1 1 calc R . . H9B H 1.2272 0.1507 0.4508 0.059 Uiso 1 1 calc R . . H9C H 1.1223 0.0685 0.4527 0.059 Uiso 1 1 calc R . . C10 C 0.8849(3) 0.1714(5) 0.48443(18) 0.0470(16) Uani 1 1 d . . . H10A H 0.8306 0.1327 0.4659 0.070 Uiso 1 1 calc R . . H10B H 0.8545 0.2053 0.5121 0.070 Uiso 1 1 calc R . . H10C H 0.9367 0.1054 0.4918 0.070 Uiso 1 1 calc R . . C11 C 0.9359(3) 0.2811(4) 0.45895(15) 0.0305(12) Uani 1 1 d . . . H11 H 0.9896 0.3188 0.4792 0.037 Uiso 1 1 calc R . . C12 C 0.8609(3) 0.3895(5) 0.44820(17) 0.0463(15) Uani 1 1 d . . . H12A H 0.8978 0.4602 0.4332 0.069 Uiso 1 1 calc R . . H12B H 0.8299 0.4219 0.4760 0.069 Uiso 1 1 calc R . . H12C H 0.8064 0.3566 0.4285 0.069 Uiso 1 1 calc R . . C13 C 0.9671(3) 0.4791(4) 0.32477(16) 0.0417(14) Uani 1 1 d . . . H13A H 0.9076 0.5026 0.3062 0.063 Uiso 1 1 calc R . . H13B H 1.0253 0.5365 0.3177 0.063 Uiso 1 1 calc R . . H13C H 0.9489 0.4884 0.3564 0.063 Uiso 1 1 calc R . . C14 C 0.9977(3) 0.3388(4) 0.31534(17) 0.0299(14) Uani 1 1 d . . . H14 H 1.0622 0.3214 0.3327 0.036 Uiso 1 1 calc R . . C15 C 1.0246(3) 0.3220(4) 0.26601(16) 0.0375(14) Uani 1 1 d . . . H15A H 1.0363 0.2299 0.2596 0.056 Uiso 1 1 calc R . . H15B H 1.0874 0.3713 0.2591 0.056 Uiso 1 1 calc R . . H15C H 0.9674 0.3540 0.2476 0.056 Uiso 1 1 calc R . . C16 C 0.8051(3) 0.1229(5) 0.27886(15) 0.0441(16) Uani 1 1 d . . . H16A H 0.8669 0.1075 0.2607 0.066 Uiso 1 1 calc R . . H16B H 0.7447 0.1309 0.2592 0.066 Uiso 1 1 calc R . . H16C H 0.7949 0.0501 0.2995 0.066 Uiso 1 1 calc R . . C17 C 0.8186(3) 0.2479(4) 0.30558(16) 0.0294(13) Uani 1 1 d . . . H17 H 0.8235 0.3205 0.2835 0.035 Uiso 1 1 calc R . . C18 C 0.7243(3) 0.2760(4) 0.33562(16) 0.0411(15) Uani 1 1 d . . . H18A H 0.7111 0.2011 0.3550 0.062 Uiso 1 1 calc R . . H18B H 0.6635 0.2923 0.3168 0.062 Uiso 1 1 calc R . . H18C H 0.7383 0.3526 0.3541 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 P1 0.0246(6) 0.0234(9) 0.0316(12) 0.0022(6) 0.0009(5) 0.0000(4) F1 0.0450(16) 0.036(2) 0.042(2) 0.0085(13) 0.0114(13) -0.0051(11) F2 0.0631(17) 0.025(2) 0.065(3) 0.0090(15) -0.0040(14) -0.0015(12) F3 0.0498(17) 0.028(2) 0.079(3) -0.0065(14) -0.0082(14) 0.0108(14) F4 0.0393(17) 0.053(3) 0.054(3) -0.0084(14) 0.0105(13) 0.0096(11) F5 0.0419(15) 0.037(2) 0.045(3) 0.0087(14) 0.0112(11) 0.0035(11) N1 0.028(2) 0.033(3) 0.013(3) -0.0037(17) -0.0003(15) -0.0002(13) N2 0.022(2) 0.029(3) 0.028(4) 0.0059(17) -0.0061(15) -0.0029(14) C1 0.024(3) 0.028(4) 0.030(4) -0.004(2) -0.007(2) -0.0017(16) C2 0.036(3) 0.027(4) 0.028(5) -0.002(2) 0.000(2) -0.004(2) C3 0.039(3) 0.017(4) 0.047(5) 0.008(2) -0.011(2) -0.008(2) C4 0.035(3) 0.020(4) 0.059(6) -0.011(3) -0.015(2) 0.008(2) C5 0.030(3) 0.028(4) 0.046(5) -0.009(2) -0.001(2) 0.002(2) C6 0.030(3) 0.029(4) 0.030(5) 0.004(2) -0.003(2) 0.001(2) C7 0.038(3) 0.036(4) 0.042(5) -0.006(2) -0.003(2) -0.006(2) C8 0.027(2) 0.028(4) 0.034(4) -0.001(2) -0.0020(19) -0.0012(17) C9 0.034(3) 0.044(4) 0.040(5) 0.006(2) -0.011(2) 0.0007(19) C10 0.065(3) 0.042(4) 0.033(6) 0.004(3) 0.016(2) 0.005(2) C11 0.038(3) 0.038(4) 0.016(4) -0.003(2) 0.005(2) -0.0018(18) C12 0.058(4) 0.044(4) 0.037(5) -0.002(3) 0.011(2) 0.016(2) C13 0.043(3) 0.028(4) 0.055(5) 0.003(2) -0.005(2) -0.006(2) C14 0.029(3) 0.033(4) 0.028(5) 0.003(2) 0.001(2) -0.0026(18) C15 0.038(3) 0.048(4) 0.026(5) 0.007(2) 0.003(2) -0.0041(19) C16 0.038(3) 0.043(5) 0.051(5) -0.007(2) -0.004(2) -0.0036(19) C17 0.030(2) 0.028(4) 0.031(5) 0.005(2) -0.006(2) 0.0024(18) C18 0.028(3) 0.051(5) 0.044(5) 0.003(2) -0.006(2) 0.0053(18) _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 1.669(4) . ? P1 N1 1.683(3) . ? P1 C1 1.896(5) . ? F1 C2 1.351(5) . ? F2 C3 1.350(5) . ? F3 C4 1.347(5) . ? F4 C5 1.344(5) . ? F5 C6 1.354(5) . ? N1 C8 1.477(4) . ? N1 C11 1.493(5) . ? N2 C14 1.481(5) . ? N2 C17 1.513(5) . ? C1 C2 1.385(6) . ? C1 C6 1.387(6) . ? C2 C3 1.375(6) . ? C3 C4 1.379(7) . ? C4 C5 1.366(7) . ? C5 C6 1.379(6) . ? C7 C8 1.532(6) . ? C8 C9 1.542(6) . ? C10 C11 1.514(6) . ? C11 C12 1.515(6) . ? C13 C14 1.525(6) . ? C14 C15 1.524(6) . ? C16 C17 1.526(5) . ? C17 C18 1.542(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 N2 P1 N1 109.17(19) . . ? N2 P1 C1 108.0(2) . . ? N1 P1 C1 98.41(18) . . ? C8 N1 C11 116.3(3) . . ? C8 N1 P1 125.5(3) . . ? C11 N1 P1 117.3(3) . . ? C14 N2 C17 114.4(4) . . ? C14 N2 P1 128.3(3) . . ? C17 N2 P1 116.9(3) . . ? C2 C1 C6 114.2(4) . . ? C2 C1 P1 115.5(4) . . ? C6 C1 P1 130.3(4) . . ? F1 C2 C3 116.1(5) . . ? F1 C2 C1 119.9(4) . . ? C3 C2 C1 124.0(5) . . ? F2 C3 C2 121.1(5) . . ? F2 C3 C4 119.6(4) . . ? C2 C3 C4 119.3(5) . . ? F3 C4 C5 121.0(5) . . ? F3 C4 C3 119.9(5) . . ? C5 C4 C3 119.1(5) . . ? F4 C5 C4 119.6(4) . . ? F4 C5 C6 120.4(5) . . ? C4 C5 C6 120.0(5) . . ? F5 C6 C5 116.1(5) . . ? F5 C6 C1 120.4(4) . . ? C5 C6 C1 123.4(5) . . ? N1 C8 C7 112.8(4) . . ? N1 C8 C9 112.1(3) . . ? C7 C8 C9 110.3(4) . . ? N1 C11 C10 112.9(4) . . ? N1 C11 C12 111.1(4) . . ? C10 C11 C12 112.2(4) . . ? N2 C14 C15 114.3(4) . . ? N2 C14 C13 111.2(3) . . ? C15 C14 C13 110.2(4) . . ? N2 C17 C16 111.6(3) . . ? N2 C17 C18 111.8(4) . . ? C16 C17 C18 111.9(3) . . ? _diffrn_measured_fraction_theta_max 0.270 _diffrn_reflns_theta_full 26.31 _diffrn_measured_fraction_theta_full 0.270 _refine_diff_density_max 0.092 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.023