Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Evamarie Hey-Hawkins' 'Gennadii P. Belov' 'Andrey A. Karasik' 'Peter Lonnecke' 'Roman N. Naumov' 'Helena V. Novikova' 'Oleg G. Sinyashin' _publ_contact_author_name 'Prof Evamarie Hey-Hawkins' _publ_contact_author_address ; Fakultat fur Chemie und Mineralogie Universitat Leipzig Johannisallee 29 04103 Leipzig Sachsen GERMANY ; _publ_contact_author_email HEY@RZ.UNI-LEIPZIG.DE _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Novel chiral 1,5-diaza-3,7-diphosphacyclooctane ligands and their transition metal complexes ; #------------------------------------------------------------------------------# # DATA BLOCK # #------------------------------------------------------------------------------# data_c988_fin _database_code_CSD 200855 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H36 N2 P2' _chemical_formula_weight 510.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source P P 0.1023 0.0942 '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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 23.052(12) _cell_length_b 5.472(3) _cell_length_c 22.567(12) _cell_angle_alpha 90.00 _cell_angle_beta 100.552(10) _cell_angle_gamma 90.00 _cell_volume 2799(2) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 1200 _cell_measurement_theta_min 2.326 _cell_measurement_theta_max 24.089 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.179 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9911 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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-Diffractometer (AXS Bruker)' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8210 _diffrn_reflns_av_R_equivalents 0.0678 _diffrn_reflns_av_sigmaI/netI 0.1257 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 0.92 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5349 _reflns_number_gt 3256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (AXS Bruker)' _computing_cell_refinement 'SAINT (AXS Bruker)' _computing_data_reduction 'SAINT (AXS Bruker)' _computing_structure_solution 'SHESXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (AXS Bruker)' _computing_publication_material ? _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^)+(0.0661P)^2^+3.3458P] 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 -0.01(17) _refine_ls_number_reflns 5349 _refine_ls_number_parameters 367 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1378 _refine_ls_R_factor_gt 0.0718 _refine_ls_wR_factor_ref 0.1758 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 P1A P 0.57202(6) 0.0607(3) 0.52047(6) 0.0391(4) Uani 1 1 d . . . P1B P 0.56219(6) 0.7524(3) 0.98159(6) 0.0347(4) Uani 1 1 d . . . N1A N 0.51069(19) 0.2151(10) 0.40518(19) 0.0395(12) Uani 1 1 d . . . N1B N 0.45607(18) 0.9270(9) 0.90441(18) 0.0356(11) Uani 1 1 d . . . C1A C 0.5607(3) 0.2678(15) 0.4525(3) 0.0444(15) Uani 1 1 d . . . C2A C 0.5457(2) 0.2676(13) 0.5781(2) 0.0408(14) Uani 1 1 d . . . C3A C 0.6508(2) 0.0952(12) 0.5482(3) 0.0427(15) Uani 1 1 d . . . C4A C 0.6865(3) 0.2852(15) 0.5357(3) 0.0611(19) Uani 1 1 d . . . H4A H 0.6699 0.4119 0.5099 0.073 Uiso 1 1 calc R . . C5A C 0.7463(3) 0.2927(16) 0.5603(3) 0.073(2) Uani 1 1 d . . . H5A H 0.7698 0.4211 0.5501 0.088 Uiso 1 1 calc R . . C6A C 0.7713(3) 0.1152(16) 0.5991(3) 0.070(2) Uani 1 1 d . . . H6A H 0.8115 0.1238 0.6165 0.084 Uiso 1 1 calc R . . C7A C 0.7377(3) -0.0756(17) 0.6127(3) 0.077(2) Uani 1 1 d . . . H7A H 0.7547 -0.1984 0.6394 0.092 Uiso 1 1 calc R . . C8A C 0.6783(3) -0.0869(15) 0.5867(3) 0.067(2) Uani 1 1 d . . . H8A H 0.6559 -0.2214 0.5954 0.080 Uiso 1 1 calc R . . C9A C 0.5120(3) -0.0225(13) 0.3754(3) 0.0490(17) Uani 1 1 d . . . C10A C 0.4664(2) -0.0246(11) 0.3174(2) 0.0395(14) Uani 1 1 d . . . C11A C 0.4274(3) -0.2154(12) 0.3052(3) 0.0487(15) Uani 1 1 d . . . H11A H 0.4286 -0.3447 0.3328 0.058 Uiso 1 1 calc R . . C12A C 0.3863(3) -0.2172(13) 0.2519(3) 0.0527(16) Uani 1 1 d . . . H12A H 0.3596 -0.3482 0.2438 0.063 Uiso 1 1 calc R . . C13A C 0.3839(3) -0.0317(12) 0.2109(3) 0.0475(16) Uani 1 1 d . . . H13A H 0.3559 -0.0330 0.1750 0.057 Uiso 1 1 calc R . . C14A C 0.4233(3) 0.1556(11) 0.2238(2) 0.0452(16) Uani 1 1 d . . . H14A H 0.4226 0.2831 0.1957 0.054 Uiso 1 1 calc R . . C15A C 0.4640(3) 0.1631(11) 0.2764(2) 0.0439(16) Uani 1 1 d . . . H15A H 0.4901 0.2960 0.2845 0.053 Uiso 1 1 calc R . . C16A C 0.5728(3) -0.0841(18) 0.3611(3) 0.083(3) Uani 1 1 d . . . H16A H 0.5882 0.0566 0.3429 0.124 Uiso 1 1 calc R . . H16B H 0.5693 -0.2210 0.3334 0.124 Uiso 1 1 calc R . . H16C H 0.5995 -0.1270 0.3981 0.124 Uiso 1 1 calc R . . C1B C 0.5190(2) 0.9741(12) 0.9243(3) 0.0399(15) Uani 1 1 d . . . C2B C 0.5790(3) 0.9635(12) 1.0488(2) 0.0358(13) Uani 1 1 d . . . C3B C 0.6326(2) 0.7491(11) 0.9544(2) 0.0334(12) Uani 1 1 d . . . C4B C 0.6435(2) 0.5457(12) 0.9216(2) 0.0389(13) Uani 1 1 d . . . H4B H 0.6154 0.4193 0.9156 0.047 Uiso 1 1 calc R . . C5B C 0.6939(2) 0.5222(11) 0.8974(2) 0.0417(14) Uani 1 1 d . . . H5B H 0.6990 0.3858 0.8736 0.050 Uiso 1 1 calc R . . C6B C 0.7371(2) 0.7006(12) 0.9086(2) 0.0450(16) Uani 1 1 d . . . H6B H 0.7721 0.6845 0.8931 0.054 Uiso 1 1 calc R . . C7B C 0.7285(2) 0.9004(12) 0.9422(2) 0.0397(14) Uani 1 1 d . . . H7B H 0.7579 1.0210 0.9505 0.048 Uiso 1 1 calc R . . C8B C 0.6765(2) 0.9258(11) 0.9643(2) 0.0360(13) Uani 1 1 d . . . H8B H 0.6709 1.0661 0.9866 0.043 Uiso 1 1 calc R . . C9B C 0.4385(2) 0.7038(11) 0.8692(2) 0.0380(14) Uani 1 1 d . . . C10B C 0.3774(2) 0.7418(12) 0.8314(2) 0.0378(13) Uani 1 1 d . . . C11B C 0.3337(3) 0.5728(16) 0.8309(3) 0.0643(19) Uani 1 1 d . . . H11B H 0.3409 0.4365 0.8566 0.077 Uiso 1 1 calc R . . C12B C 0.2791(3) 0.597(2) 0.7937(3) 0.083(3) Uani 1 1 d . . . H12B H 0.2500 0.4763 0.7938 0.100 Uiso 1 1 calc R . . C13B C 0.2677(3) 0.7937(19) 0.7572(3) 0.075(2) Uani 1 1 d . . . H13B H 0.2307 0.8114 0.7319 0.090 Uiso 1 1 calc R . . C14B C 0.3108(4) 0.9677(19) 0.7576(4) 0.096(3) Uani 1 1 d . . . H14B H 0.3033 1.1059 0.7326 0.116 Uiso 1 1 calc R . . C15B C 0.3657(3) 0.9394(15) 0.7949(3) 0.068(2) Uani 1 1 d . . . H15B H 0.3949 1.0590 0.7948 0.081 Uiso 1 1 calc R . . C16B C 0.4821(3) 0.6358(13) 0.8284(3) 0.057(2) Uani 1 1 d . . . H16D H 0.4868 0.7731 0.8025 0.085 Uiso 1 1 calc R . . H16E H 0.4672 0.4961 0.8038 0.085 Uiso 1 1 calc R . . H16F H 0.5199 0.5951 0.8530 0.085 Uiso 1 1 calc R . . H1A H 0.596(3) 0.260(14) 0.439(3) 0.07(2) Uiso 1 1 d . . . H1B H 0.5581(19) 0.419(10) 0.466(2) 0.020(14) Uiso 1 1 d . . . H2A H 0.5797(19) 0.272(9) 0.612(2) 0.023(12) Uiso 1 1 d . . . H2B H 0.541(2) 0.450(12) 0.559(3) 0.059(18) Uiso 1 1 d . . . H9A H 0.506(2) -0.143(11) 0.402(3) 0.043(19) Uiso 1 1 d . . . H1C H 0.520(3) 1.152(13) 0.943(3) 0.07(2) Uiso 1 1 d . . . H1D H 0.539(2) 0.975(9) 0.887(2) 0.032(14) Uiso 1 1 d . . . H2C H 0.621(2) 0.936(10) 1.068(2) 0.035(14) Uiso 1 1 d . . . H2D H 0.574(2) 1.145(12) 1.031(3) 0.057(19) Uiso 1 1 d . . . H9B H 0.4383(19) 0.558(11) 0.895(2) 0.032(13) Uiso 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 P1A 0.0430(9) 0.0438(9) 0.0289(8) -0.0022(8) 0.0023(6) -0.0050(8) P1B 0.0352(8) 0.0405(9) 0.0279(7) -0.0011(7) 0.0041(6) -0.0041(7) N1A 0.043(3) 0.049(3) 0.024(2) -0.001(2) 0.0018(19) 0.004(2) N1B 0.036(3) 0.042(3) 0.026(2) -0.001(2) -0.0019(19) -0.003(2) C1A 0.053(4) 0.048(4) 0.031(3) -0.001(4) 0.005(3) -0.002(4) C2A 0.042(3) 0.050(4) 0.029(3) 0.001(3) 0.002(2) -0.009(3) C3A 0.042(3) 0.049(4) 0.036(3) -0.005(3) 0.007(2) -0.002(3) C4A 0.057(4) 0.061(5) 0.059(4) 0.006(4) -0.003(3) -0.017(4) C5A 0.048(4) 0.090(6) 0.080(5) -0.002(5) 0.008(4) -0.032(4) C6A 0.050(4) 0.091(7) 0.062(5) 0.000(4) -0.007(3) -0.005(4) C7A 0.056(5) 0.094(7) 0.070(5) 0.019(5) -0.013(4) 0.002(5) C8A 0.050(4) 0.077(6) 0.066(5) 0.019(4) -0.008(3) -0.012(4) C9A 0.057(4) 0.056(5) 0.031(3) -0.003(3) 0.003(3) 0.012(3) C10A 0.043(3) 0.048(4) 0.028(3) -0.001(3) 0.008(2) 0.011(3) C11A 0.067(4) 0.039(4) 0.041(3) 0.003(3) 0.011(3) -0.002(4) C12A 0.056(4) 0.047(4) 0.056(4) -0.010(4) 0.011(3) -0.019(4) C13A 0.044(4) 0.058(5) 0.038(3) -0.003(3) 0.002(3) 0.005(3) C14A 0.056(4) 0.046(4) 0.030(3) 0.007(3) -0.002(3) -0.005(3) C15A 0.051(4) 0.047(4) 0.031(3) -0.001(3) 0.001(3) -0.009(3) C16A 0.055(4) 0.127(7) 0.060(5) -0.025(5) -0.006(3) 0.033(5) C1B 0.036(3) 0.050(4) 0.031(3) 0.003(3) -0.002(2) -0.010(3) C2B 0.038(3) 0.042(4) 0.025(3) 0.001(3) 0.001(2) -0.010(3) C3B 0.034(3) 0.036(3) 0.029(3) 0.003(3) 0.001(2) -0.004(3) C4B 0.041(3) 0.037(3) 0.037(3) 0.000(3) 0.004(2) -0.001(3) C5B 0.046(3) 0.041(4) 0.037(3) 0.002(3) 0.006(3) 0.007(3) C6B 0.036(3) 0.060(5) 0.039(3) 0.008(3) 0.007(3) 0.003(3) C7B 0.028(3) 0.048(4) 0.042(3) 0.007(3) 0.003(2) -0.003(3) C8B 0.038(3) 0.039(3) 0.030(3) 0.002(3) 0.005(2) 0.001(3) C9B 0.038(3) 0.042(4) 0.033(3) 0.001(3) 0.003(2) 0.001(3) C10B 0.037(3) 0.047(4) 0.027(3) 0.000(3) 0.000(2) -0.006(3) C11B 0.049(4) 0.074(5) 0.064(4) 0.003(4) -0.003(3) -0.024(4) C12B 0.039(4) 0.132(8) 0.075(5) -0.016(6) 0.002(4) -0.025(5) C13B 0.050(5) 0.116(8) 0.051(4) -0.015(5) -0.013(3) 0.022(5) C14B 0.105(7) 0.100(8) 0.066(5) 0.008(5) -0.032(5) 0.007(6) C15B 0.060(4) 0.073(5) 0.058(4) 0.016(4) -0.022(3) -0.011(4) C16B 0.044(4) 0.078(6) 0.049(4) -0.017(3) 0.009(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 P1A C3A 1.819(6) . ? P1A C1A 1.887(7) . ? P1A C2A 1.906(6) . ? P1B C3B 1.838(5) . ? P1B C2B 1.889(6) . ? P1B C1B 1.915(6) . ? N1A C2A 1.447(7) 2_656 ? N1A C1A 1.450(7) . ? N1A C9A 1.467(8) . ? N1B C2B 1.457(7) 2_657 ? N1B C1B 1.461(7) . ? N1B C9B 1.474(7) . ? C2A N1A 1.447(7) 2_656 ? C3A C4A 1.388(9) . ? C3A C8A 1.396(9) . ? C4A C5A 1.389(8) . ? C5A C6A 1.363(10) . ? C6A C7A 1.368(10) . ? C7A C8A 1.387(9) . ? C9A C10A 1.520(8) . ? C9A C16A 1.533(9) . ? C10A C11A 1.373(8) . ? C10A C15A 1.377(8) . ? C11A C12A 1.388(8) . ? C12A C13A 1.368(8) . ? C13A C14A 1.366(8) . ? C14A C15A 1.374(7) . ? C2B N1B 1.457(7) 2_657 ? C3B C4B 1.384(8) . ? C3B C8B 1.388(8) . ? C4B C5B 1.378(7) . ? C5B C6B 1.384(8) . ? C6B C7B 1.367(8) . ? C7B C8B 1.386(7) . ? C9B C10B 1.521(7) . ? C9B C16B 1.528(7) . ? C10B C15B 1.356(9) . ? C10B C11B 1.366(9) . ? C11B C12B 1.387(9) . ? C12B C13B 1.353(12) . ? C13B C14B 1.375(12) . ? C14B C15B 1.394(9) . ? 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 C3A P1A C1A 101.4(3) . . ? C3A P1A C2A 97.2(3) . . ? C1A P1A C2A 100.6(3) . . ? C3B P1B C2B 102.1(3) . . ? C3B P1B C1B 99.3(3) . . ? C2B P1B C1B 99.2(3) . . ? C2A N1A C1A 113.6(5) 2_656 . ? C2A N1A C9A 113.0(5) 2_656 . ? C1A N1A C9A 115.7(5) . . ? C2B N1B C1B 113.9(4) 2_657 . ? C2B N1B C9B 111.7(5) 2_657 . ? C1B N1B C9B 118.2(5) . . ? N1A C1A P1A 116.9(5) . . ? N1A C2A P1A 118.2(4) 2_656 . ? C4A C3A C8A 116.3(6) . . ? C4A C3A P1A 126.9(5) . . ? C8A C3A P1A 116.8(5) . . ? C3A C4A C5A 121.6(7) . . ? C6A C5A C4A 120.4(7) . . ? C5A C6A C7A 119.9(7) . . ? C6A C7A C8A 119.6(7) . . ? C7A C8A C3A 122.1(7) . . ? N1A C9A C10A 109.4(5) . . ? N1A C9A C16A 112.8(6) . . ? C10A C9A C16A 109.4(5) . . ? C11A C10A C15A 119.2(5) . . ? C11A C10A C9A 120.2(6) . . ? C15A C10A C9A 120.6(6) . . ? C10A C11A C12A 119.9(6) . . ? C13A C12A C11A 121.1(6) . . ? C14A C13A C12A 118.1(5) . . ? C13A C14A C15A 121.9(6) . . ? C14A C15A C10A 119.8(6) . . ? N1B C1B P1B 117.4(4) . . ? N1B C2B P1B 116.0(4) 2_657 . ? C4B C3B C8B 116.7(5) . . ? C4B C3B P1B 116.3(4) . . ? C8B C3B P1B 127.0(4) . . ? C5B C4B C3B 122.3(6) . . ? C4B C5B C6B 119.5(6) . . ? C7B C6B C5B 119.5(5) . . ? C6B C7B C8B 120.2(6) . . ? C7B C8B C3B 121.6(5) . . ? N1B C9B C10B 108.9(5) . . ? N1B C9B C16B 112.4(5) . . ? C10B C9B C16B 109.9(4) . . ? C15B C10B C11B 118.1(6) . . ? C15B C10B C9B 120.7(5) . . ? C11B C10B C9B 121.1(6) . . ? C10B C11B C12B 121.8(8) . . ? C13B C12B C11B 119.8(8) . . ? C12B C13B C14B 119.3(7) . . ? C13B C14B C15B 120.1(8) . . ? C10B C15B C14B 120.9(7) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.266 _refine_diff_density_min -0.240 _refine_diff_density_rms 0.056 #------------------------------------------------------------------------------# # END OF DATA BLOCK # #------------------------------------------------------------------------------#