# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Gareth Rowlands' 'Martyn Coles' 'Jean E. Glover' 'Peter B Hitchcock' 'Richard J. Seacome' _publ_contact_author_name 'Gareth Rowlands' _publ_contact_author_email G.J.ROWLANDS@MASSEY.AC.NZ _publ_section_title ; Planar-chiral imidazole-based phosphine ligands derived from [2.2]paracyclophane ; _publ_requested_category FO # Attachment 'GJR_Dalton_oct09.cif' data_(1)-oct1007 _database_code_depnum_ccdc_archive 'CCDC 753893' #TrackingRef 'GJR_Dalton_oct09.cif' _audit_creation_date 2007-10-12T09:32:02-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H35 N2 P' _chemical_formula_sum 'C27 H35 N2 P' _chemical_formula_weight 418.54 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4500(6) _cell_length_b 11.6495(9) _cell_length_c 12.9271(8) _cell_angle_alpha 109.719(4) _cell_angle_beta 90.305(5) _cell_angle_gamma 98.638(3) _cell_volume 1182.17(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 29958 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.176 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.7936E-2 _diffrn_orient_matrix_ub_12 -0.460617E-1 _diffrn_orient_matrix_ub_13 -0.810832E-1 _diffrn_orient_matrix_ub_21 -0.161005E-1 _diffrn_orient_matrix_ub_22 0.76891E-1 _diffrn_orient_matrix_ub_23 -0.14052E-1 _diffrn_orient_matrix_ub_31 0.118567 _diffrn_orient_matrix_ub_32 0.224464E-1 _diffrn_orient_matrix_ub_33 -0.23254E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0909 _diffrn_reflns_av_unetI/netI 0.0723 _diffrn_reflns_number 16283 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.54 _diffrn_reflns_theta_max 25.93 _diffrn_reflns_theta_full 25.93 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.985 _reflns_number_total 4541 _reflns_number_gt 3240 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0442P)^2^+0.9460P] 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_number_reflns 4541 _refine_ls_number_parameters 277 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1398 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.208 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.049 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P P 0.74256(8) 0.67899(6) 0.83394(5) 0.02803(19) Uani 1 1 d . . . N1 N 0.6412(2) 0.45403(19) 0.66294(15) 0.0280(5) Uani 1 1 d . . . N2 N 0.8526(3) 0.5654(2) 0.62099(17) 0.0340(5) Uani 1 1 d . . . C1 C 0.6425(4) 0.2114(3) 0.8222(3) 0.0482(8) Uani 1 1 d . . . H1A H 0.7413 0.1813 0.7906 0.058 Uiso 1 1 calc R . . H1B H 0.629 0.1941 0.8918 0.058 Uiso 1 1 calc R . . C2 C 0.6637(3) 0.3552(3) 0.8483(2) 0.0370(7) Uani 1 1 d . . . H2A H 0.6886 0.3978 0.9283 0.044 Uiso 1 1 calc R . . H2B H 0.7559 0.3805 0.8094 0.044 Uiso 1 1 calc R . . C3 C 0.5166(3) 0.3962(2) 0.81445(19) 0.0295(6) Uani 1 1 d . . . C4 C 0.5023(3) 0.4215(2) 0.71683(19) 0.0268(5) Uani 1 1 d . . . C5 C 0.3529(3) 0.4024(2) 0.6625(2) 0.0304(6) Uani 1 1 d . . . H5 H 0.346 0.4168 0.5946 0.036 Uiso 1 1 calc R . . C6 C 0.2150(3) 0.3629(2) 0.7056(2) 0.0330(6) Uani 1 1 d . . . C7 C 0.2275(3) 0.3688(2) 0.8145(2) 0.0366(6) Uani 1 1 d . . . H7 H 0.1331 0.3617 0.853 0.044 Uiso 1 1 calc R . . C8 C 0.3757(3) 0.3848(2) 0.8676(2) 0.0347(6) Uani 1 1 d . . . H8 H 0.3814 0.388 0.942 0.042 Uiso 1 1 calc R . . C9 C 0.0668(4) 0.2939(3) 0.6323(3) 0.0468(8) Uani 1 1 d . . . H9A H 0.0577 0.328 0.5723 0.056 Uiso 1 1 calc R . . H9B H -0.029 0.3074 0.6759 0.056 Uiso 1 1 calc R . . C10 C 0.0689(4) 0.1511(3) 0.5804(3) 0.0494(8) Uani 1 1 d . . . H10A H -0.0307 0.1061 0.5976 0.059 Uiso 1 1 calc R . . H10B H 0.0692 0.128 0.4994 0.059 Uiso 1 1 calc R . . C11 C 0.2109(4) 0.1102(2) 0.6208(2) 0.0396(7) Uani 1 1 d . . . C12 C 0.3579(4) 0.1192(2) 0.5737(2) 0.0412(7) Uani 1 1 d . . . H12 H 0.3605 0.1157 0.4992 0.049 Uiso 1 1 calc R . . C13 C 0.5004(4) 0.1332(2) 0.6333(2) 0.0411(7) Uani 1 1 d . . . H13 H 0.5993 0.138 0.5992 0.049 Uiso 1 1 calc R . . C14 C 0.4998(4) 0.1402(2) 0.7423(2) 0.0389(7) Uani 1 1 d . . . C15 C 0.3553(4) 0.1036(3) 0.7799(2) 0.0401(7) Uani 1 1 d . . . H15 H 0.354 0.0889 0.8479 0.048 Uiso 1 1 calc R . . C16 C 0.2112(4) 0.0879(2) 0.7203(2) 0.0405(7) Uani 1 1 d . . . H16 H 0.1129 0.0618 0.7474 0.049 Uiso 1 1 calc R . . C17 C 0.7519(3) 0.5620(2) 0.69892(19) 0.0268(5) Uani 1 1 d . . . C18 C 0.8032(3) 0.4585(3) 0.5329(2) 0.0348(6) Uani 1 1 d . . . H18 H 0.8532 0.4359 0.4648 0.042 Uiso 1 1 calc R . . C19 C 0.6750(3) 0.3909(2) 0.55645(19) 0.0321(6) Uani 1 1 d . . . H19 H 0.6183 0.3142 0.5089 0.039 Uiso 1 1 calc R . . C20 C 0.6528(3) 0.7977(2) 0.7925(2) 0.0347(6) Uani 1 1 d . . . C21 C 0.6170(4) 0.8983(3) 0.8960(2) 0.0538(9) Uani 1 1 d . . . H21A H 0.718 0.9457 0.9359 0.081 Uiso 1 1 calc R . . H21B H 0.554 0.8606 0.9431 0.081 Uiso 1 1 calc R . . H21C H 0.556 0.9535 0.8757 0.081 Uiso 1 1 calc R . . C22 C 0.7481(6) 0.8572(4) 0.7200(4) 0.0856(14) Uani 1 1 d . . . H22A H 0.6833 0.9085 0.697 0.128 Uiso 1 1 calc R . . H22B H 0.7766 0.7929 0.6548 0.128 Uiso 1 1 calc R . . H22C H 0.846 0.9089 0.7612 0.128 Uiso 1 1 calc R . . C23 C 0.4936(4) 0.7283(3) 0.7314(3) 0.0712(12) Uani 1 1 d . . . H23A H 0.4339 0.7863 0.7145 0.107 Uiso 1 1 calc R . . H23B H 0.4308 0.6893 0.7777 0.107 Uiso 1 1 calc R . . H23C H 0.5137 0.6647 0.6628 0.107 Uiso 1 1 calc R . . C24 C 0.9604(3) 0.7343(2) 0.8814(2) 0.0363(6) Uani 1 1 d . . . C25 C 1.0236(4) 0.6193(3) 0.8853(3) 0.0732(12) Uani 1 1 d . . . H25A H 1.1308 0.6436 0.9226 0.11 Uiso 1 1 calc R . . H25B H 1.0292 0.5625 0.8101 0.11 Uiso 1 1 calc R . . H25C H 0.9512 0.5781 0.9256 0.11 Uiso 1 1 calc R . . C26 C 0.9651(4) 0.8242(3) 0.9999(2) 0.0442(7) Uani 1 1 d . . . H26A H 0.8965 0.7852 1.0437 0.066 Uiso 1 1 calc R . . H26B H 0.9264 0.8994 1 0.066 Uiso 1 1 calc R . . H26C H 1.0756 0.8455 1.032 0.066 Uiso 1 1 calc R . . C27 C 1.0700(4) 0.7969(4) 0.8152(3) 0.0691(11) Uani 1 1 d . . . H27A H 1.1813 0.8104 0.8439 0.104 Uiso 1 1 calc R . . H27B H 1.0382 0.8764 0.8217 0.104 Uiso 1 1 calc R . . H27C H 1.0604 0.7438 0.7376 0.104 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 P 0.0315(4) 0.0290(4) 0.0240(3) 0.0098(3) 0.0010(3) 0.0045(3) N1 0.0314(12) 0.0307(12) 0.0222(10) 0.0094(9) 0.0013(9) 0.0048(9) N2 0.0358(13) 0.0387(13) 0.0292(12) 0.0127(10) 0.0067(10) 0.0085(10) C1 0.0482(18) 0.0470(19) 0.0572(19) 0.0266(15) -0.0069(15) 0.0106(15) C2 0.0406(16) 0.0415(16) 0.0310(14) 0.0166(12) -0.0074(12) 0.0037(13) C3 0.0378(15) 0.0240(13) 0.0237(12) 0.0063(10) -0.0021(11) 0.0010(11) C4 0.0299(14) 0.0246(13) 0.0241(12) 0.0059(10) 0.0037(10) 0.0047(10) C5 0.0367(15) 0.0285(14) 0.0283(13) 0.0106(11) 0.0000(11) 0.0100(11) C6 0.0310(15) 0.0244(14) 0.0443(16) 0.0121(12) 0.0020(12) 0.0062(11) C7 0.0383(16) 0.0295(15) 0.0444(16) 0.0146(12) 0.0130(13) 0.0082(12) C8 0.0465(17) 0.0291(14) 0.0280(13) 0.0098(11) 0.0069(12) 0.0044(12) C9 0.0353(16) 0.0463(18) 0.061(2) 0.0221(15) -0.0033(14) 0.0049(14) C10 0.0500(19) 0.0469(19) 0.0472(18) 0.0156(15) -0.0129(14) -0.0029(15) C11 0.0510(18) 0.0248(14) 0.0365(15) 0.0051(12) -0.0073(13) -0.0004(13) C12 0.064(2) 0.0310(16) 0.0253(14) 0.0048(12) 0.0016(13) 0.0080(14) C13 0.0532(19) 0.0300(15) 0.0416(16) 0.0107(12) 0.0099(14) 0.0148(13) C14 0.0491(18) 0.0264(15) 0.0450(17) 0.0146(12) 0.0000(13) 0.0121(13) C15 0.0554(19) 0.0330(15) 0.0368(15) 0.0176(12) -0.0001(14) 0.0084(14) C16 0.0497(18) 0.0286(15) 0.0417(16) 0.0127(12) 0.0039(13) 0.0005(13) C17 0.0265(13) 0.0293(14) 0.0263(12) 0.0112(11) 0.0022(10) 0.0059(11) C18 0.0395(16) 0.0438(17) 0.0238(13) 0.0126(12) 0.0058(11) 0.0124(13) C19 0.0394(16) 0.0343(15) 0.0212(13) 0.0072(11) 0.0007(11) 0.0071(12) C20 0.0453(17) 0.0344(15) 0.0280(13) 0.0123(11) 0.0036(12) 0.0137(12) C21 0.079(2) 0.0443(19) 0.0381(17) 0.0067(14) -0.0036(16) 0.0287(17) C22 0.120(4) 0.091(3) 0.093(3) 0.074(3) 0.055(3) 0.062(3) C23 0.070(2) 0.048(2) 0.086(3) 0.0053(19) -0.038(2) 0.0225(18) C24 0.0332(15) 0.0345(16) 0.0373(15) 0.0075(12) -0.0072(12) 0.0048(12) C25 0.061(2) 0.048(2) 0.093(3) -0.0017(19) -0.041(2) 0.0200(17) C26 0.0484(18) 0.0391(17) 0.0411(16) 0.0124(13) -0.0105(13) -0.0011(14) C27 0.0417(19) 0.096(3) 0.051(2) 0.0110(19) 0.0068(15) -0.0150(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 P C17 1.828(2) . ? P C24 1.883(3) . ? P C20 1.893(3) . ? N1 C19 1.379(3) . ? N1 C17 1.386(3) . ? N1 C4 1.435(3) . ? N2 C17 1.329(3) . ? N2 C18 1.380(3) . ? C1 C14 1.522(4) . ? C1 C2 1.576(4) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.509(4) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C8 1.389(4) . ? C3 C4 1.398(3) . ? C4 C5 1.392(3) . ? C5 C6 1.379(4) . ? C5 H5 0.95 . ? C6 C7 1.390(4) . ? C6 C9 1.511(4) . ? C7 C8 1.381(4) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.573(4) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.507(4) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.391(4) . ? C11 C16 1.397(4) . ? C12 C13 1.385(4) . ? C12 H12 0.95 . ? C13 C14 1.384(4) . ? C13 H13 0.95 . ? C14 C15 1.377(4) . ? C15 C16 1.393(4) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C18 C19 1.340(4) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C22 1.513(4) . ? C20 C21 1.519(4) . ? C20 C23 1.522(4) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C25 1.530(4) . ? C24 C27 1.532(4) . ? C24 C26 1.533(4) . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? 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 C17 P C24 102.69(12) . . ? C17 P C20 100.34(11) . . ? C24 P C20 111.47(13) . . ? C19 N1 C17 106.5(2) . . ? C19 N1 C4 125.2(2) . . ? C17 N1 C4 127.5(2) . . ? C17 N2 C18 105.7(2) . . ? C14 C1 C2 113.2(2) . . ? C14 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? C14 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 112.9(2) . . ? C3 C2 H2A 109 . . ? C1 C2 H2A 109 . . ? C3 C2 H2B 109 . . ? C1 C2 H2B 109 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 115.8(2) . . ? C8 C3 C2 120.0(2) . . ? C4 C3 C2 122.8(2) . . ? C5 C4 C3 120.6(2) . . ? C5 C4 N1 117.7(2) . . ? C3 C4 N1 121.3(2) . . ? C6 C5 C4 121.0(2) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 116.8(2) . . ? C5 C6 C9 121.1(2) . . ? C7 C6 C9 121.1(3) . . ? C8 C7 C6 120.8(3) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C3 121.4(2) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C6 C9 C10 112.8(2) . . ? C6 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? C6 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 113.8(2) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C12 C11 C16 116.5(3) . . ? C12 C11 C10 120.9(3) . . ? C16 C11 C10 121.2(3) . . ? C13 C12 C11 121.2(3) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 117.1(3) . . ? C15 C14 C1 121.0(3) . . ? C13 C14 C1 120.5(3) . . ? C14 C15 C16 121.3(3) . . ? C14 C15 H15 119.4 . . ? C16 C15 H15 119.4 . . ? C15 C16 C11 120.1(3) . . ? C15 C16 H16 120 . . ? C11 C16 H16 120 . . ? N2 C17 N1 110.2(2) . . ? N2 C17 P 128.52(19) . . ? N1 C17 P 121.22(17) . . ? C19 C18 N2 110.7(2) . . ? C19 C18 H18 124.6 . . ? N2 C18 H18 124.6 . . ? C18 C19 N1 106.8(2) . . ? C18 C19 H19 126.6 . . ? N1 C19 H19 126.6 . . ? C22 C20 C21 108.9(3) . . ? C22 C20 C23 108.7(3) . . ? C21 C20 C23 107.9(3) . . ? C22 C20 P 117.5(2) . . ? C21 C20 P 108.70(18) . . ? C23 C20 P 104.6(2) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C27 109.8(3) . . ? C25 C24 C26 107.6(2) . . ? C27 C24 C26 108.4(2) . . ? C25 C24 P 104.7(2) . . ? C27 C24 P 119.0(2) . . ? C26 C24 P 106.72(19) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? #===END data_(2)-oct1107 _database_code_depnum_ccdc_archive 'CCDC 753894' #TrackingRef 'GJR_Dalton_oct09.cif' _audit_creation_date 2007-10-15T08:59:15-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C31 H39 N2 P' _chemical_formula_sum 'C31 H39 N2 P' _chemical_formula_weight 470.61 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.7792(3) _cell_length_b 15.7625(8) _cell_length_c 15.3052(7) _cell_angle_alpha 90 _cell_angle_beta 97.193(3) _cell_angle_gamma 90 _cell_volume 2580.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 18878 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_diffrn 1.212 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_special_details ; Very weak diffraction ! ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.129 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.373773E-1 _diffrn_orient_matrix_ub_12 -0.578584E-1 _diffrn_orient_matrix_ub_13 -0.9315E-2 _diffrn_orient_matrix_ub_21 -0.833337E-1 _diffrn_orient_matrix_ub_22 0.230394E-1 _diffrn_orient_matrix_ub_23 0.104103E-1 _diffrn_orient_matrix_ub_31 -0.02005 _diffrn_orient_matrix_ub_32 0.121013E-1 _diffrn_orient_matrix_ub_33 -0.643568E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.2298 _diffrn_reflns_av_unetI/netI 0.1408 _diffrn_reflns_number 39349 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 26 _diffrn_reflns_theta_full 26 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _reflns_number_total 5049 _reflns_number_gt 2851 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0249P)^2^+4.8595P] 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_number_reflns 5049 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1847 _refine_ls_R_factor_gt 0.0947 _refine_ls_wR_factor_ref 0.1684 _refine_ls_wR_factor_gt 0.141 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.305 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.067 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P P 0.60330(9) 0.12171(7) 0.47553(7) 0.0251(3) Uani 1 1 d . . . N1 N 0.5024(3) 0.2800(2) 0.5207(2) 0.0258(8) Uani 1 1 d . . . N2 N 0.7098(3) 0.2795(2) 0.5286(3) 0.0379(10) Uani 1 1 d . . . C1 C 0.3253(6) 0.3165(3) 0.3020(4) 0.0655(17) Uani 1 1 d . . . H1A H 0.4011 0.3519 0.3015 0.079 Uiso 1 1 calc R . . H1B H 0.2896 0.3068 0.24 0.079 Uiso 1 1 calc R . . C2 C 0.3640(4) 0.2305(3) 0.3441(3) 0.0354(12) Uani 1 1 d . . . H2A H 0.3308 0.1847 0.3035 0.042 Uiso 1 1 calc R . . H2B H 0.4564 0.2264 0.3514 0.042 Uiso 1 1 calc R . . C3 C 0.3189(4) 0.2161(3) 0.4323(3) 0.0270(10) Uani 1 1 d . . . C4 C 0.3743(3) 0.2519(3) 0.5110(3) 0.0230(10) Uani 1 1 d . . . C5 C 0.3032(4) 0.2721(3) 0.5783(3) 0.0278(10) Uani 1 1 d . . . H5 H 0.3421 0.2985 0.6305 0.033 Uiso 1 1 calc R . . C6 C 0.1754(4) 0.2539(3) 0.5697(3) 0.0290(10) Uani 1 1 d . . . C7 C 0.1291(4) 0.1996(3) 0.5024(3) 0.0320(11) Uani 1 1 d . . . H7 H 0.0489 0.1746 0.5026 0.038 Uiso 1 1 calc R . . C8 C 0.1999(4) 0.1813(3) 0.4341(3) 0.0311(11) Uani 1 1 d . . . H8 H 0.1664 0.1444 0.388 0.037 Uiso 1 1 calc R . . C9 C 0.0879(4) 0.3057(3) 0.6186(3) 0.0430(13) Uani 1 1 d . . . H9A H 0.1354 0.3282 0.6732 0.052 Uiso 1 1 calc R . . H9B H 0.0216 0.268 0.6358 0.052 Uiso 1 1 calc R . . C10 C 0.0253(5) 0.3812(3) 0.5639(3) 0.0516(14) Uani 1 1 d . . . H10A H -0.0652 0.3694 0.5498 0.062 Uiso 1 1 calc R . . H10B H 0.0346 0.4332 0.6004 0.062 Uiso 1 1 calc R . . C11 C 0.0797(4) 0.3971(3) 0.4796(3) 0.0356(11) Uani 1 1 d . . . C12 C 0.1963(4) 0.4349(3) 0.4812(3) 0.0347(11) Uani 1 1 d . . . H12 H 0.2255 0.4722 0.5281 0.042 Uiso 1 1 calc R . . C13 C 0.2703(4) 0.4194(3) 0.4159(3) 0.0353(11) Uani 1 1 d . . . H13 H 0.3491 0.4467 0.418 0.042 Uiso 1 1 calc R . . C14 C 0.2317(5) 0.3648(3) 0.3476(3) 0.0370(12) Uani 1 1 d . . . C15 C 0.1050(5) 0.3439(3) 0.3366(3) 0.0469(14) Uani 1 1 d . . . H15 H 0.0688 0.3185 0.2831 0.056 Uiso 1 1 calc R . . C16 C 0.0308(4) 0.3594(3) 0.4027(3) 0.0436(13) Uani 1 1 d . . . H16 H -0.0549 0.3437 0.3943 0.052 Uiso 1 1 calc R . . C17 C 0.6075(4) 0.2332(3) 0.5085(3) 0.0266(10) Uani 1 1 d . . . C18 C 0.6691(4) 0.3577(3) 0.5546(3) 0.0401(12) Uani 1 1 d . . . H18 H 0.7223 0.4043 0.5724 0.048 Uiso 1 1 calc R . . C19 C 0.5435(4) 0.3587(3) 0.5514(3) 0.0344(11) Uani 1 1 d . . . H19 H 0.4934 0.4044 0.5671 0.041 Uiso 1 1 calc R . . C20 C 0.6476(3) 0.0697(3) 0.5840(3) 0.0274(10) Uani 1 1 d . . . H20 H 0.6519 0.0074 0.5721 0.033 Uiso 1 1 calc R . . C21 C 0.7721(4) 0.0935(3) 0.6376(3) 0.0421(13) Uani 1 1 d . . . H21A H 0.8411 0.0839 0.6017 0.05 Uiso 1 1 calc R . . H21B H 0.7714 0.1545 0.6531 0.05 Uiso 1 1 calc R . . C22 C 0.7945(4) 0.0410(3) 0.7212(3) 0.0473(13) Uani 1 1 d . . . H22A H 0.8732 0.0595 0.7564 0.057 Uiso 1 1 calc R . . H22B H 0.8038 -0.0194 0.7056 0.057 Uiso 1 1 calc R . . C23 C 0.6865(5) 0.0502(4) 0.7764(3) 0.0593(16) Uani 1 1 d . . . H23A H 0.7015 0.0128 0.8286 0.071 Uiso 1 1 calc R . . H23B H 0.6829 0.1094 0.7973 0.071 Uiso 1 1 calc R . . C24 C 0.5628(5) 0.0271(3) 0.7236(3) 0.0515(14) Uani 1 1 d . . . H24A H 0.4942 0.036 0.76 0.062 Uiso 1 1 calc R . . H24B H 0.5634 -0.0336 0.7069 0.062 Uiso 1 1 calc R . . C25 C 0.5405(4) 0.0819(3) 0.6405(3) 0.0356(11) Uani 1 1 d . . . H25A H 0.5355 0.1424 0.6573 0.043 Uiso 1 1 calc R . . H25B H 0.4601 0.0659 0.6059 0.043 Uiso 1 1 calc R . . C26 C 0.7495(3) 0.1187(3) 0.4233(3) 0.0267(10) Uani 1 1 d . . . H26 H 0.8179 0.1467 0.4634 0.032 Uiso 1 1 calc R . . C27 C 0.7863(4) 0.0261(3) 0.4083(3) 0.0312(11) Uani 1 1 d . . . H27A H 0.7162 -0.0032 0.3725 0.037 Uiso 1 1 calc R . . H27B H 0.8024 -0.0034 0.4657 0.037 Uiso 1 1 calc R . . C28 C 0.9039(4) 0.0211(3) 0.3609(3) 0.0339(11) Uani 1 1 d . . . H28A H 0.9762 0.0448 0.3994 0.041 Uiso 1 1 calc R . . H28B H 0.9224 -0.039 0.3489 0.041 Uiso 1 1 calc R . . C29 C 0.8855(4) 0.0699(3) 0.2751(3) 0.0427(12) Uani 1 1 d . . . H29A H 0.8196 0.042 0.2341 0.051 Uiso 1 1 calc R . . H29B H 0.964 0.0686 0.2478 0.051 Uiso 1 1 calc R . . C30 C 0.8487(4) 0.1613(3) 0.2887(3) 0.0354(11) Uani 1 1 d . . . H30A H 0.833 0.1901 0.2309 0.042 Uiso 1 1 calc R . . H30B H 0.9183 0.191 0.3244 0.042 Uiso 1 1 calc R . . C31 C 0.7310(4) 0.1665(3) 0.3353(3) 0.0328(11) Uani 1 1 d . . . H31A H 0.6593 0.1418 0.2969 0.039 Uiso 1 1 calc R . . H31B H 0.7115 0.2268 0.3459 0.039 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 P 0.0186(5) 0.0252(7) 0.0321(6) -0.0027(5) 0.0051(4) 0.0008(5) N1 0.0192(17) 0.025(2) 0.034(2) -0.0053(17) 0.0045(15) 0.0042(15) N2 0.026(2) 0.027(2) 0.061(3) -0.009(2) 0.0046(18) -0.0033(17) C1 0.115(5) 0.043(4) 0.048(3) -0.001(3) 0.048(3) 0.002(3) C2 0.030(2) 0.051(3) 0.026(2) -0.008(2) 0.0022(19) 0.011(2) C3 0.024(2) 0.027(3) 0.031(2) -0.002(2) 0.0045(19) 0.0061(19) C4 0.019(2) 0.024(2) 0.025(2) 0.0047(19) 0.0015(18) 0.0065(17) C5 0.030(2) 0.031(3) 0.023(2) 0.002(2) 0.0035(18) 0.006(2) C6 0.027(2) 0.033(3) 0.027(2) 0.013(2) 0.0074(19) 0.008(2) C7 0.023(2) 0.027(3) 0.047(3) 0.008(2) 0.004(2) -0.0032(19) C8 0.030(2) 0.024(3) 0.037(3) -0.006(2) 0.000(2) 0.002(2) C9 0.031(3) 0.064(4) 0.037(3) 0.009(3) 0.019(2) 0.016(2) C10 0.053(3) 0.050(3) 0.057(3) -0.001(3) 0.026(3) 0.021(3) C11 0.038(3) 0.024(3) 0.045(3) 0.001(2) 0.006(2) 0.013(2) C12 0.050(3) 0.023(3) 0.028(3) -0.002(2) -0.005(2) 0.006(2) C13 0.048(3) 0.021(3) 0.036(3) 0.006(2) 0.000(2) 0.000(2) C14 0.065(3) 0.019(3) 0.029(3) 0.007(2) 0.011(2) 0.002(2) C15 0.080(4) 0.029(3) 0.026(3) 0.003(2) -0.016(3) -0.003(3) C16 0.040(3) 0.034(3) 0.053(3) 0.006(3) -0.010(3) 0.005(2) C17 0.024(2) 0.024(3) 0.033(2) 0.000(2) 0.0061(19) 0.0014(19) C18 0.031(3) 0.028(3) 0.060(3) -0.008(2) -0.001(2) -0.007(2) C19 0.035(3) 0.025(3) 0.043(3) -0.013(2) 0.003(2) -0.003(2) C20 0.024(2) 0.026(3) 0.033(2) -0.003(2) 0.0052(18) 0.0003(19) C21 0.033(3) 0.044(3) 0.047(3) -0.004(2) -0.005(2) 0.001(2) C22 0.048(3) 0.048(3) 0.043(3) -0.008(3) -0.007(2) 0.009(3) C23 0.094(5) 0.057(4) 0.025(3) 0.004(3) 0.001(3) 0.018(3) C24 0.065(4) 0.051(4) 0.043(3) 0.006(3) 0.024(3) 0.013(3) C25 0.036(3) 0.035(3) 0.037(3) -0.003(2) 0.012(2) 0.004(2) C26 0.022(2) 0.025(3) 0.034(2) 0.001(2) 0.0087(18) -0.0005(19) C27 0.026(2) 0.032(3) 0.038(3) 0.004(2) 0.011(2) 0.0006(19) C28 0.034(2) 0.029(3) 0.042(3) -0.004(2) 0.017(2) 0.006(2) C29 0.045(3) 0.042(3) 0.045(3) -0.008(3) 0.020(2) 0.001(2) C30 0.042(3) 0.032(3) 0.034(3) 0.003(2) 0.012(2) -0.001(2) C31 0.032(2) 0.029(3) 0.039(3) 0.006(2) 0.011(2) 0.003(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 P C17 1.828(4) . ? P C26 1.855(4) . ? P C20 1.860(4) . ? N1 C19 1.380(5) . ? N1 C17 1.384(5) . ? N1 C4 1.439(5) . ? N2 C17 1.327(5) . ? N2 C18 1.383(6) . ? C1 C14 1.504(7) . ? C1 C2 1.536(7) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.507(6) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C4 1.395(5) . ? C3 C8 1.399(6) . ? C4 C5 1.397(5) . ? C5 C6 1.398(5) . ? C5 H5 0.95 . ? C6 C7 1.383(6) . ? C6 C9 1.514(6) . ? C7 C8 1.399(6) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.558(6) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.503(6) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C16 1.363(6) . ? C11 C12 1.389(6) . ? C12 C13 1.376(6) . ? C12 H12 0.95 . ? C13 C14 1.378(6) . ? C13 H13 0.95 . ? C14 C15 1.395(7) . ? C15 C16 1.387(7) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C18 C19 1.348(6) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C21 1.529(6) . ? C20 C25 1.539(5) . ? C20 H20 1 . ? C21 C22 1.518(6) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 C23 1.527(7) . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? C23 C24 1.514(7) . ? C23 H23A 0.99 . ? C23 H23B 0.99 . ? C24 C25 1.533(6) . ? C24 H24A 0.99 . ? C24 H24B 0.99 . ? C25 H25A 0.99 . ? C25 H25B 0.99 . ? C26 C31 1.536(6) . ? C26 C27 1.538(6) . ? C26 H26 1 . ? C27 C28 1.539(5) . ? C27 H27A 0.99 . ? C27 H27B 0.99 . ? C28 C29 1.513(6) . ? C28 H28A 0.99 . ? C28 H28B 0.99 . ? C29 C30 1.516(6) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 C31 1.533(6) . ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? C31 H31A 0.99 . ? C31 H31B 0.99 . ? 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 C17 P C26 98.63(19) . . ? C17 P C20 100.55(19) . . ? C26 P C20 103.66(18) . . ? C19 N1 C17 106.9(3) . . ? C19 N1 C4 125.1(3) . . ? C17 N1 C4 127.8(3) . . ? C17 N2 C18 105.8(3) . . ? C14 C1 C2 114.5(4) . . ? C14 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? C14 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 114.0(4) . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? H2A C2 H2B 107.6 . . ? C4 C3 C8 115.8(4) . . ? C4 C3 C2 124.1(4) . . ? C8 C3 C2 118.5(4) . . ? C3 C4 C5 121.0(4) . . ? C3 C4 N1 121.0(3) . . ? C5 C4 N1 117.5(3) . . ? C6 C5 C4 120.6(4) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 117.2(4) . . ? C7 C6 C9 120.8(4) . . ? C5 C6 C9 120.6(4) . . ? C6 C7 C8 120.3(4) . . ? C6 C7 H7 119.9 . . ? C8 C7 H7 119.9 . . ? C3 C8 C7 121.5(4) . . ? C3 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C6 C9 C10 113.7(4) . . ? C6 C9 H9A 108.8 . . ? C10 C9 H9A 108.8 . . ? C6 C9 H9B 108.8 . . ? C10 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? C11 C10 C9 113.5(4) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C16 C11 C12 116.9(4) . . ? C16 C11 C10 121.2(5) . . ? C12 C11 C10 120.4(4) . . ? C13 C12 C11 121.1(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C12 C13 C14 121.0(4) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C13 C14 C15 115.9(4) . . ? C13 C14 C1 120.8(5) . . ? C15 C14 C1 121.9(5) . . ? C16 C15 C14 121.0(4) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C11 C16 C15 120.7(5) . . ? C11 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? N2 C17 N1 110.3(4) . . ? N2 C17 P 125.8(3) . . ? N1 C17 P 123.8(3) . . ? C19 C18 N2 110.7(4) . . ? C19 C18 H18 124.7 . . ? N2 C18 H18 124.7 . . ? C18 C19 N1 106.3(4) . . ? C18 C19 H19 126.8 . . ? N1 C19 H19 126.8 . . ? C21 C20 C25 109.7(4) . . ? C21 C20 P 118.7(3) . . ? C25 C20 P 108.6(3) . . ? C21 C20 H20 106.4 . . ? C25 C20 H20 106.4 . . ? P C20 H20 106.4 . . ? C22 C21 C20 110.7(4) . . ? C22 C21 H21A 109.5 . . ? C20 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 108.1 . . ? C21 C22 C23 111.2(4) . . ? C21 C22 H22A 109.4 . . ? C23 C22 H22A 109.4 . . ? C21 C22 H22B 109.4 . . ? C23 C22 H22B 109.4 . . ? H22A C22 H22B 108 . . ? C24 C23 C22 111.3(4) . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108 . . ? C23 C24 C25 110.1(4) . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24A 109.7 . . ? C23 C24 H24B 109.7 . . ? C25 C24 H24B 109.7 . . ? H24A C24 H24B 108.2 . . ? C24 C25 C20 110.2(4) . . ? C24 C25 H25A 109.6 . . ? C20 C25 H25A 109.6 . . ? C24 C25 H25B 109.6 . . ? C20 C25 H25B 109.6 . . ? H25A C25 H25B 108.1 . . ? C31 C26 C27 110.0(3) . . ? C31 C26 P 110.0(3) . . ? C27 C26 P 109.7(3) . . ? C31 C26 H26 109 . . ? C27 C26 H26 109 . . ? P C26 H26 109 . . ? C26 C27 C28 111.2(3) . . ? C26 C27 H27A 109.4 . . ? C28 C27 H27A 109.4 . . ? C26 C27 H27B 109.4 . . ? C28 C27 H27B 109.4 . . ? H27A C27 H27B 108 . . ? C29 C28 C27 110.9(4) . . ? C29 C28 H28A 109.5 . . ? C27 C28 H28A 109.5 . . ? C29 C28 H28B 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 108 . . ? C28 C29 C30 111.9(4) . . ? C28 C29 H29A 109.2 . . ? C30 C29 H29A 109.2 . . ? C28 C29 H29B 109.2 . . ? C30 C29 H29B 109.2 . . ? H29A C29 H29B 107.9 . . ? C29 C30 C31 111.2(4) . . ? C29 C30 H30A 109.4 . . ? C31 C30 H30A 109.4 . . ? C29 C30 H30B 109.4 . . ? C31 C30 H30B 109.4 . . ? H30A C30 H30B 108 . . ? C30 C31 C26 110.9(3) . . ? C30 C31 H31A 109.5 . . ? C26 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C26 C31 H31B 109.5 . . ? H31A C31 H31B 108 . . ? #===END data_(3)-jan808 _database_code_depnum_ccdc_archive 'CCDC 753895' #TrackingRef 'GJR_Dalton_oct09.cif' _audit_creation_date 2008-01-14T10:55:39-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H35 N2 O P, 0.5(C6 H12)' _chemical_formula_sum 'C30 H41 N2 O P' _chemical_formula_weight 476.62 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1186(3) _cell_length_b 11.6152(3) _cell_length_c 13.9871(4) _cell_angle_alpha 105.127(1) _cell_angle_beta 105.574(2) _cell_angle_gamma 102.542(2) _cell_volume 1310.24(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10388 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.208 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.13 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.11235 _diffrn_orient_matrix_ub_12 0.20079E-2 _diffrn_orient_matrix_ub_13 -0.27018E-1 _diffrn_orient_matrix_ub_21 -0.04095 _diffrn_orient_matrix_ub_22 -0.922963E-1 _diffrn_orient_matrix_ub_23 -0.148763E-1 _diffrn_orient_matrix_ub_31 -0.53105E-2 _diffrn_orient_matrix_ub_32 0.164309E-1 _diffrn_orient_matrix_ub_33 0.72629E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_unetI/netI 0.0372 _diffrn_reflns_number 18924 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 5112 _reflns_number_gt 4188 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0729P)^2^+1.2169P] 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_number_reflns 5112 _refine_ls_number_parameters 313 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0686 _refine_ls_R_factor_gt 0.0543 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1426 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.868 _refine_diff_density_min -0.692 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 P P 0.36043(6) 0.17290(5) 0.27134(4) 0.02125(17) Uani 1 1 d . . . O O 0.40850(18) 0.27203(14) 0.37549(12) 0.0269(4) Uani 1 1 d . . . N1 N 0.5248(2) 0.33610(17) 0.18402(14) 0.0241(4) Uani 1 1 d . . . N2 N 0.3245(2) 0.16852(19) 0.06813(15) 0.0324(5) Uani 1 1 d . . . C1 C 0.4584(3) 0.6600(2) 0.3252(2) 0.0360(6) Uani 1 1 d . . . H1A H 0.3674 0.6511 0.2632 0.043 Uiso 1 1 calc R . . H1B H 0.4492 0.7165 0.3884 0.043 Uiso 1 1 calc R . . C2 C 0.4459(3) 0.5269(2) 0.3375(2) 0.0291(5) Uani 1 1 d . . . H2A H 0.4071 0.5228 0.3965 0.035 Uiso 1 1 calc R . . H2B H 0.3664 0.4613 0.2722 0.035 Uiso 1 1 calc R . . C3 C 0.6041(2) 0.50006(19) 0.35798(17) 0.0221(4) Uani 1 1 d . . . C4 C 0.6449(2) 0.42536(19) 0.28003(17) 0.0218(4) Uani 1 1 d . . . C5 C 0.8044(3) 0.4460(2) 0.28600(19) 0.0258(5) Uani 1 1 d . . . H5 H 0.8296 0.3961 0.2309 0.031 Uiso 1 1 calc R . . C6 C 0.9263(3) 0.5390(2) 0.37190(19) 0.0265(5) Uani 1 1 d . . . C7 C 0.8873(3) 0.5904(2) 0.45987(18) 0.0264(5) Uani 1 1 d . . . H7 H 0.9702 0.6389 0.5254 0.032 Uiso 1 1 calc R . . C8 C 0.7289(3) 0.5712(2) 0.45259(18) 0.0250(5) Uani 1 1 d . . . H8 H 0.7048 0.6074 0.5134 0.03 Uiso 1 1 calc R . . C9 C 1.0835(3) 0.5993(2) 0.3628(2) 0.0347(6) Uani 1 1 d . . . H9A H 1.1031 0.5392 0.3066 0.042 Uiso 1 1 calc R . . H9B H 1.1708 0.6184 0.43 0.042 Uiso 1 1 calc R . . C10 C 1.0879(3) 0.7248(3) 0.3365(2) 0.0408(6) Uani 1 1 d . . . H10A H 1.1715 0.7959 0.3957 0.049 Uiso 1 1 calc R . . H10B H 1.1178 0.7183 0.2727 0.049 Uiso 1 1 calc R . . C11 C 0.9297(3) 0.7520(2) 0.3179(2) 0.0312(5) Uani 1 1 d . . . C12 C 0.8027(3) 0.6846(2) 0.2245(2) 0.0335(6) Uani 1 1 d . . . H12 H 0.8233 0.6487 0.1621 0.04 Uiso 1 1 calc R . . C13 C 0.6455(3) 0.6689(2) 0.22101(19) 0.0307(5) Uani 1 1 d . . . H13 H 0.5597 0.6233 0.1562 0.037 Uiso 1 1 calc R . . C14 C 0.6131(3) 0.7196(2) 0.31181(19) 0.0282(5) Uani 1 1 d . . . C15 C 0.7394(3) 0.8087(2) 0.39716(19) 0.0295(5) Uani 1 1 d . . . H15 H 0.7182 0.8591 0.4541 0.035 Uiso 1 1 calc R . . C16 C 0.8968(3) 0.8254(2) 0.4007(2) 0.0311(5) Uani 1 1 d . . . H16 H 0.982 0.887 0.4597 0.037 Uiso 1 1 calc R . . C17 C 0.4034(3) 0.2316(2) 0.16967(17) 0.0241(5) Uani 1 1 d . . . C18 C 0.3965(3) 0.2337(2) 0.01526(19) 0.0356(6) Uani 1 1 d . . . H18 H 0.3645 0.2106 -0.0593 0.043 Uiso 1 1 calc R . . C19 C 0.5195(3) 0.3357(2) 0.08445(18) 0.0318(5) Uani 1 1 d . . . H19 H 0.5884 0.3951 0.0676 0.038 Uiso 1 1 calc R . . C20 C 0.4801(3) 0.0633(2) 0.28142(19) 0.0303(5) Uani 1 1 d . . . C21 C 0.4400(4) -0.0034(3) 0.3563(3) 0.0542(8) Uani 1 1 d . . . H21A H 0.3311 -0.0621 0.3225 0.081 Uiso 1 1 calc R . . H21B H 0.4473 0.0587 0.4215 0.081 Uiso 1 1 calc R . . H21C H 0.516 -0.0495 0.3728 0.081 Uiso 1 1 calc R . . C22 C 0.4621(5) -0.0315(3) 0.1773(3) 0.0637(10) Uani 1 1 d . . . H22A H 0.5383 -0.0784 0.19 0.096 Uiso 1 1 calc R . . H22B H 0.4835 0.0126 0.1292 0.096 Uiso 1 1 calc R . . H22C H 0.3528 -0.0897 0.1457 0.096 Uiso 1 1 calc R . . C23 C 0.6548(3) 0.1469(3) 0.3329(3) 0.0549(8) Uani 1 1 d . . . H23A H 0.724 0.0959 0.35 0.082 Uiso 1 1 calc R . . H23B H 0.667 0.2123 0.3976 0.082 Uiso 1 1 calc R . . H23C H 0.6851 0.1859 0.2839 0.082 Uiso 1 1 calc R . . C24 C 0.1400(3) 0.0970(2) 0.21886(19) 0.0295(5) Uani 1 1 d . . . C25 C 0.0892(3) 0.0783(3) 0.3114(2) 0.0385(6) Uani 1 1 d . . . H25A H -0.0277 0.044 0.2875 0.058 Uiso 1 1 calc R . . H25B H 0.1249 0.1592 0.3684 0.058 Uiso 1 1 calc R . . H25C H 0.1378 0.0199 0.3372 0.058 Uiso 1 1 calc R . . C26 C 0.0794(3) -0.0287(3) 0.1284(2) 0.0441(7) Uani 1 1 d . . . H26A H 0.1139 -0.092 0.1551 0.066 Uiso 1 1 calc R . . H26B H 0.1233 -0.0193 0.0731 0.066 Uiso 1 1 calc R . . H26C H -0.0378 -0.0551 0.0991 0.066 Uiso 1 1 calc R . . C27 C 0.0632(3) 0.1911(3) 0.1823(2) 0.0425(7) Uani 1 1 d . . . H27A H 0.0865 0.1999 0.1197 0.064 Uiso 1 1 calc R . . H27B H 0.1072 0.2727 0.239 0.064 Uiso 1 1 calc R . . H27C H -0.0529 0.1604 0.165 0.064 Uiso 1 1 calc R . . C28 C -0.0821(5) 0.3813(3) -0.0096(3) 0.0610(9) Uani 1 1 d . . . H28A H -0.1133 0.3343 -0.0857 0.073 Uiso 1 1 calc R . . H28B H -0.1214 0.3221 0.0243 0.073 Uiso 1 1 calc R . . C29 C 0.0943(4) 0.4325(3) 0.0373(3) 0.0587(9) Uani 1 1 d . . . H29A H 0.1259 0.4711 0.1148 0.07 Uiso 1 1 calc R . . H29B H 0.1412 0.3633 0.0231 0.07 Uiso 1 1 calc R . . C30 C 0.1549(3) 0.5218(2) -0.0035(2) 0.0362(6) Uani 1 1 d . . . H30A H 0.1346 0.4812 -0.0794 0.043 Uiso 1 1 calc R . . H30B H 0.2721 0.5583 0.0331 0.043 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 P 0.0233(3) 0.0184(3) 0.0218(3) 0.0068(2) 0.0085(2) 0.0051(2) O 0.0321(8) 0.0216(8) 0.0242(8) 0.0041(6) 0.0123(7) 0.0040(7) N1 0.0266(9) 0.0242(9) 0.0234(9) 0.0090(8) 0.0116(8) 0.0068(8) N2 0.0367(11) 0.0320(11) 0.0226(10) 0.0076(8) 0.0077(9) 0.0042(9) C1 0.0264(12) 0.0338(13) 0.0583(17) 0.0224(12) 0.0196(12) 0.0152(10) C2 0.0233(11) 0.0263(12) 0.0445(14) 0.0138(10) 0.0188(10) 0.0101(9) C3 0.0230(10) 0.0183(10) 0.0309(12) 0.0121(9) 0.0145(9) 0.0067(8) C4 0.0236(10) 0.0191(10) 0.0261(11) 0.0107(9) 0.0108(9) 0.0069(8) C5 0.0269(11) 0.0236(11) 0.0356(13) 0.0131(10) 0.0178(10) 0.0121(9) C6 0.0216(11) 0.0255(11) 0.0393(13) 0.0167(10) 0.0122(10) 0.0115(9) C7 0.0278(11) 0.0217(11) 0.0294(12) 0.0125(9) 0.0058(10) 0.0074(9) C8 0.0322(12) 0.0209(11) 0.0277(12) 0.0120(9) 0.0146(10) 0.0097(9) C9 0.0217(11) 0.0319(13) 0.0527(16) 0.0158(12) 0.0141(11) 0.0094(10) C10 0.0290(13) 0.0399(14) 0.0657(19) 0.0278(14) 0.0256(13) 0.0107(11) C11 0.0311(12) 0.0287(12) 0.0466(15) 0.0244(11) 0.0217(11) 0.0094(10) C12 0.0438(14) 0.0326(13) 0.0390(14) 0.0209(11) 0.0251(12) 0.0165(11) C13 0.0336(12) 0.0275(12) 0.0336(13) 0.0165(10) 0.0088(10) 0.0105(10) C14 0.0284(11) 0.0259(11) 0.0417(14) 0.0208(10) 0.0149(10) 0.0160(10) C15 0.0364(13) 0.0237(11) 0.0373(13) 0.0142(10) 0.0173(11) 0.0157(10) C16 0.0322(12) 0.0214(11) 0.0406(14) 0.0141(10) 0.0121(11) 0.0060(10) C17 0.0253(11) 0.0225(11) 0.0245(11) 0.0084(9) 0.0092(9) 0.0059(9) C18 0.0452(14) 0.0381(14) 0.0242(12) 0.0114(10) 0.0142(11) 0.0106(12) C19 0.0401(13) 0.0327(13) 0.0285(12) 0.0136(10) 0.0187(11) 0.0099(11) C20 0.0349(13) 0.0282(12) 0.0346(13) 0.0133(10) 0.0153(11) 0.0156(10) C21 0.067(2) 0.0558(18) 0.080(2) 0.0510(18) 0.0438(18) 0.0392(16) C22 0.089(3) 0.058(2) 0.0518(19) 0.0070(16) 0.0257(18) 0.0496(19) C23 0.0320(14) 0.0533(18) 0.088(2) 0.0365(18) 0.0162(15) 0.0205(13) C24 0.0252(11) 0.0275(12) 0.0327(13) 0.0130(10) 0.0066(10) 0.0031(9) C25 0.0307(13) 0.0400(14) 0.0467(15) 0.0210(12) 0.0167(12) 0.0030(11) C26 0.0404(15) 0.0363(14) 0.0357(15) 0.0080(12) 0.0007(12) -0.0064(12) C27 0.0261(12) 0.0497(16) 0.0600(18) 0.0320(14) 0.0131(12) 0.0138(12) C28 0.096(3) 0.0380(16) 0.0541(19) 0.0131(14) 0.0416(19) 0.0130(17) C29 0.078(2) 0.064(2) 0.058(2) 0.0315(17) 0.0328(18) 0.0428(19) C30 0.0379(13) 0.0369(14) 0.0449(15) 0.0210(12) 0.0223(12) 0.0147(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 P O 1.4841(15) . ? P C17 1.825(2) . ? P C20 1.857(2) . ? P C24 1.859(2) . ? N1 C19 1.379(3) . ? N1 C17 1.381(3) . ? N1 C4 1.438(3) . ? N2 C17 1.323(3) . ? N2 C18 1.374(3) . ? C1 C14 1.513(3) . ? C1 C2 1.583(3) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.510(3) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C8 1.393(3) . ? C3 C4 1.394(3) . ? C4 C5 1.398(3) . ? C5 C6 1.390(3) . ? C5 H5 0.95 . ? C6 C7 1.393(3) . ? C6 C9 1.506(3) . ? C7 C8 1.384(3) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.589(3) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.512(3) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C12 1.386(4) . ? C11 C16 1.393(3) . ? C12 C13 1.392(3) . ? C12 H12 0.95 . ? C13 C14 1.390(3) . ? C13 H13 0.95 . ? C14 C15 1.386(3) . ? C15 C16 1.391(3) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C18 C19 1.356(4) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C22 1.521(4) . ? C20 C21 1.528(4) . ? C20 C23 1.532(4) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C26 1.532(3) . ? C24 C25 1.537(3) . ? C24 C27 1.542(3) . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C28 C30 1.422(4) 2_565 ? C28 C29 1.479(5) . ? C28 H28A 0.99 . ? C28 H28B 0.99 . ? C29 C30 1.392(4) . ? C29 H29A 0.99 . ? C29 H29B 0.99 . ? C30 C28 1.422(4) 2_565 ? C30 H30A 0.99 . ? C30 H30B 0.99 . ? 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 O P C17 113.85(9) . . ? O P C20 109.85(10) . . ? C17 P C20 103.49(10) . . ? O P C24 110.16(10) . . ? C17 P C24 104.67(10) . . ? C20 P C24 114.69(11) . . ? C19 N1 C17 106.23(18) . . ? C19 N1 C4 124.07(18) . . ? C17 N1 C4 129.53(18) . . ? C17 N2 C18 105.7(2) . . ? C14 C1 C2 113.35(18) . . ? C14 C1 H1A 108.9 . . ? C2 C1 H1A 108.9 . . ? C14 C1 H1B 108.9 . . ? C2 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C3 C2 C1 112.50(18) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 116.05(19) . . ? C8 C3 C2 119.24(19) . . ? C4 C3 C2 123.5(2) . . ? C3 C4 C5 120.9(2) . . ? C3 C4 N1 121.52(19) . . ? C5 C4 N1 117.03(19) . . ? C6 C5 C4 120.5(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 117.1(2) . . ? C5 C6 C9 121.2(2) . . ? C7 C6 C9 120.7(2) . . ? C8 C7 C6 120.6(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C3 121.4(2) . . ? C7 C8 H8 119.3 . . ? C3 C8 H8 119.3 . . ? C6 C9 C10 112.72(19) . . ? C6 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? C6 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 113.05(19) . . ? C11 C10 H10A 109 . . ? C9 C10 H10A 109 . . ? C11 C10 H10B 109 . . ? C9 C10 H10B 109 . . ? H10A C10 H10B 107.8 . . ? C12 C11 C16 117.4(2) . . ? C12 C11 C10 120.5(2) . . ? C16 C11 C10 120.8(2) . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 117.2(2) . . ? C15 C14 C1 120.6(2) . . ? C13 C14 C1 120.9(2) . . ? C14 C15 C16 121.0(2) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? C15 C16 C11 120.1(2) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? N2 C17 N1 111.05(19) . . ? N2 C17 P 121.50(16) . . ? N1 C17 P 127.23(16) . . ? C19 C18 N2 110.5(2) . . ? C19 C18 H18 124.7 . . ? N2 C18 H18 124.7 . . ? C18 C19 N1 106.5(2) . . ? C18 C19 H19 126.8 . . ? N1 C19 H19 126.8 . . ? C22 C20 C21 110.6(2) . . ? C22 C20 C23 108.3(2) . . ? C21 C20 C23 108.2(2) . . ? C22 C20 P 115.62(19) . . ? C21 C20 P 108.50(17) . . ? C23 C20 P 105.20(17) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C26 C24 C25 109.4(2) . . ? C26 C24 C27 109.8(2) . . ? C25 C24 C27 107.6(2) . . ? C26 C24 P 115.39(18) . . ? C25 C24 P 107.36(16) . . ? C27 C24 P 107.05(16) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C30 C28 C29 111.4(3) 2_565 . ? C30 C28 H28A 109.3 2_565 . ? C29 C28 H28A 109.3 . . ? C30 C28 H28B 109.3 2_565 . ? C29 C28 H28B 109.3 . . ? H28A C28 H28B 108 . . ? C30 C29 C28 111.6(3) . . ? C30 C29 H29A 109.3 . . ? C28 C29 H29A 109.3 . . ? C30 C29 H29B 109.3 . . ? C28 C29 H29B 109.3 . . ? H29A C29 H29B 108 . . ? C29 C30 C28 110.8(2) . 2_565 ? C29 C30 H30A 109.5 . . ? C28 C30 H30A 109.5 2_565 . ? C29 C30 H30B 109.5 . . ? C28 C30 H30B 109.5 2_565 . ? H30A C30 H30B 108.1 . . ? #===END data_(4)-jan108 _database_code_depnum_ccdc_archive 'CCDC 753896' #TrackingRef 'GJR_Dalton_oct09.cif' _audit_creation_date 2008-01-04T12:49:48-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H35 Cl2 N2 P Pd, C H2 Cl2' _chemical_formula_sum 'C28 H37 Cl4 N2 P Pd' _chemical_formula_weight 680.77 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.7953(2) _cell_length_b 13.8315(3) _cell_length_c 13.0449(3) _cell_angle_alpha 90 _cell_angle_beta 91.366(2) _cell_angle_gamma 90 _cell_volume 1406.11(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 16113 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.022 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour 'Pale pink' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 1.119 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.7301 _exptl_absorpt_correction_T_max 0.8963 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.110405 _diffrn_orient_matrix_ub_12 -0.187404E-1 _diffrn_orient_matrix_ub_13 -0.352092E-1 _diffrn_orient_matrix_ub_21 0.641947E-1 _diffrn_orient_matrix_ub_22 -0.429278E-1 _diffrn_orient_matrix_ub_23 -0.473971E-1 _diffrn_orient_matrix_ub_31 -0.124689E-1 _diffrn_orient_matrix_ub_32 -0.550737E-1 _diffrn_orient_matrix_ub_33 0.489251E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0438 _diffrn_reflns_av_unetI/netI 0.0351 _diffrn_reflns_number 16669 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 26.07 _diffrn_reflns_theta_full 26.07 _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.992 _reflns_number_total 5426 _reflns_number_gt 5243 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The carbon of the dichloromethane was restrained with the DFIX command to have C-Cl distances initially set at 1.75 A. This carbon was left isotropic 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^)+(0.0663P)^2^+2.0650P] 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_number_reflns 5426 _refine_ls_number_parameters 320 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1067 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.022 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(3) _refine_diff_density_max 0.986 _refine_diff_density_min -0.832 _refine_diff_density_rms 0.103 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Pd1 Pd 0.32447(4) 0.17912(2) 0.45183(2) 0.02396(11) Uani 1 1 d . . . Cl1 Cl 0.21463(17) 0.30468(10) 0.35537(10) 0.0366(3) Uani 1 1 d . . . Cl2 Cl 0.51151(19) 0.12714(13) 0.32221(11) 0.0481(4) Uani 1 1 d . . . Cl3 Cl 0.1851(11) -0.0156(7) 0.2859(8) 0.261(4) Uani 1 1 d D . . Cl4 Cl -0.0692(9) 0.1265(8) 0.2574(5) 0.259(4) Uani 1 1 d D . . P P 0.17827(13) 0.20081(7) 0.59823(9) 0.0194(2) Uani 1 1 d . . . N1 N 0.3047(5) 0.0148(3) 0.7001(3) 0.0215(8) Uani 1 1 d . . . N2 N 0.3869(5) 0.0723(3) 0.5524(3) 0.0248(8) Uani 1 1 d . . . C1 C 0.5903(7) 0.0491(4) 0.9572(5) 0.0407(13) Uani 1 1 d . . . H1A H 0.7027 0.046 0.9236 0.049 Uiso 1 1 calc R . . H1B H 0.607 0.0838 1.0231 0.049 Uiso 1 1 calc R . . C2 C 0.4616(6) 0.1076(4) 0.8871(4) 0.0305(10) Uani 1 1 d . . . H2A H 0.4529 0.1743 0.9139 0.037 Uiso 1 1 calc R . . H2B H 0.5076 0.1114 0.8172 0.037 Uiso 1 1 calc R . . C3 C 0.2821(6) 0.0628(3) 0.8811(4) 0.0230(9) Uani 1 1 d . . . C4 C 0.2257(6) 0.0057(3) 0.7989(3) 0.0203(9) Uani 1 1 d . . . C5 C 0.1073(5) -0.0680(3) 0.8099(4) 0.0217(9) Uani 1 1 d . . . H5 H 0.0746 -0.107 0.7528 0.026 Uiso 1 1 calc R . . C6 C 0.0358(6) -0.0846(4) 0.9064(4) 0.0250(9) Uani 1 1 d . . . C7 C 0.0595(6) -0.0116(4) 0.9792(4) 0.0271(10) Uani 1 1 d . . . H7 H -0.0103 -0.0106 1.0379 0.032 Uiso 1 1 calc R . . C8 C 0.1821(6) 0.0592(4) 0.9678(4) 0.0276(10) Uani 1 1 d . . . H8 H 0.1986 0.1063 1.0201 0.033 Uiso 1 1 calc R . . C9 C -0.0300(6) -0.1827(4) 0.9352(4) 0.0313(11) Uani 1 1 d . . . H9A H -0.0862 -0.2128 0.8743 0.038 Uiso 1 1 calc R . . H9B H -0.1177 -0.1752 0.9883 0.038 Uiso 1 1 calc R . . C10 C 0.1162(7) -0.2522(4) 0.9773(5) 0.0391(12) Uani 1 1 d . . . H10A H 0.0821 -0.2785 1.0444 0.047 Uiso 1 1 calc R . . H10B H 0.1277 -0.3073 0.9294 0.047 Uiso 1 1 calc R . . C11 C 0.2889(6) -0.2027(3) 0.9902(4) 0.0282(10) Uani 1 1 d . . . C12 C 0.4048(6) -0.1980(3) 0.9090(4) 0.0295(10) Uani 1 1 d . . . H12 H 0.4013 -0.2459 0.8568 0.035 Uiso 1 1 calc R . . C13 C 0.5249(6) -0.1231(4) 0.9050(4) 0.0336(12) Uani 1 1 d . . . H13 H 0.6035 -0.1206 0.8505 0.04 Uiso 1 1 calc R . . C14 C 0.5297(6) -0.0535(4) 0.9790(4) 0.0306(12) Uani 1 1 d . . . C15 C 0.4416(7) -0.0700(4) 1.0697(5) 0.0353(12) Uani 1 1 d . . . H15 H 0.4614 -0.0292 1.1273 0.042 Uiso 1 1 calc R . . C16 C 0.3255(7) -0.1456(4) 1.0756(4) 0.0317(11) Uani 1 1 d . . . H16 H 0.2706 -0.1584 1.1384 0.038 Uiso 1 1 calc R . . C17 C 0.2947(5) 0.0915(3) 0.6356(3) 0.0206(9) Uani 1 1 d . . . C18 C 0.4577(7) -0.0174(4) 0.5626(4) 0.0307(10) Uani 1 1 d . . . H18 H 0.5293 -0.0489 0.5151 0.037 Uiso 1 1 calc R . . C19 C 0.4057(7) -0.0530(3) 0.6541(4) 0.0285(10) Uani 1 1 d . . . H19 H 0.4346 -0.1147 0.6816 0.034 Uiso 1 1 calc R . . C20 C -0.0542(5) 0.1715(4) 0.5939(3) 0.0280(9) Uani 1 1 d . . . C21 C -0.1487(7) 0.2522(4) 0.5348(5) 0.0378(12) Uani 1 1 d . . . H21A H -0.1397 0.3127 0.5736 0.057 Uiso 1 1 calc R . . H21B H -0.2699 0.2347 0.5253 0.057 Uiso 1 1 calc R . . H21C H -0.0969 0.2608 0.4677 0.057 Uiso 1 1 calc R . . C22 C -0.0685(8) 0.0763(4) 0.5331(5) 0.0424(14) Uani 1 1 d . . . H22A H -0.1896 0.0582 0.5248 0.064 Uiso 1 1 calc R . . H22B H -0.0064 0.0251 0.5704 0.064 Uiso 1 1 calc R . . H22C H -0.0186 0.085 0.4655 0.064 Uiso 1 1 calc R . . C23 C -0.1321(6) 0.1563(4) 0.6993(4) 0.0381(13) Uani 1 1 d . . . H23A H -0.2531 0.1383 0.6907 0.057 Uiso 1 1 calc R . . H23B H -0.123 0.2163 0.739 0.057 Uiso 1 1 calc R . . H23C H -0.07 0.1046 0.7357 0.057 Uiso 1 1 calc R . . C24 C 0.2476(6) 0.3066(3) 0.6762(4) 0.0218(9) Uani 1 1 d . . . C25 C 0.1836(7) 0.3047(4) 0.7869(4) 0.0313(11) Uani 1 1 d . . . H25A H 0.2272 0.3615 0.824 0.047 Uiso 1 1 calc R . . H25B H 0.2251 0.2459 0.8213 0.047 Uiso 1 1 calc R . . H25C H 0.0579 0.3054 0.7859 0.047 Uiso 1 1 calc R . . C26 C 0.1794(7) 0.3974(3) 0.6205(4) 0.0348(11) Uani 1 1 d . . . H26A H 0.2179 0.3972 0.5496 0.052 Uiso 1 1 calc R . . H26B H 0.2232 0.4553 0.6557 0.052 Uiso 1 1 calc R . . H26C H 0.0537 0.3975 0.6209 0.052 Uiso 1 1 calc R . . C27 C 0.4416(6) 0.3051(4) 0.6768(4) 0.0302(10) Uani 1 1 d . . . H27A H 0.486 0.3631 0.7115 0.045 Uiso 1 1 calc R . . H27B H 0.4812 0.3039 0.6061 0.045 Uiso 1 1 calc R . . H27C H 0.4833 0.2474 0.7132 0.045 Uiso 1 1 calc R . . C28 C 0.152(4) 0.102(3) 0.227(4) 0.54(4) Uiso 1 1 d D . . H28A H 0.2308 0.1515 0.2571 0.646 Uiso 1 1 calc R . . H28B H 0.1683 0.0997 0.1517 0.646 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 Pd1 0.02127(16) 0.02729(17) 0.02337(16) 0.00607(15) 0.00170(10) -0.00011(15) Cl1 0.0379(7) 0.0369(7) 0.0349(6) 0.0159(5) -0.0042(5) 0.0017(5) Cl2 0.0426(7) 0.0696(10) 0.0329(7) 0.0101(6) 0.0157(6) 0.0134(7) Cl3 0.236(7) 0.238(8) 0.314(10) -0.053(7) 0.112(7) -0.007(6) Cl4 0.176(5) 0.400(13) 0.200(6) 0.105(7) 0.006(5) -0.003(6) P 0.0153(5) 0.0188(6) 0.0242(5) 0.0024(4) 0.0006(4) 0.0004(4) N1 0.0229(19) 0.0166(17) 0.025(2) 0.0021(15) 0.0024(15) 0.0040(15) N2 0.0241(19) 0.025(2) 0.0252(19) 0.0009(16) 0.0066(15) 0.0037(15) C1 0.030(3) 0.032(3) 0.059(4) 0.013(3) -0.015(3) -0.009(2) C2 0.032(2) 0.024(2) 0.035(3) 0.007(2) -0.009(2) -0.004(2) C3 0.024(2) 0.0155(19) 0.029(2) 0.0014(17) -0.0048(17) 0.0058(17) C4 0.018(2) 0.016(2) 0.026(2) 0.0057(17) 0.0008(17) 0.0025(17) C5 0.018(2) 0.020(2) 0.027(2) 0.0013(17) -0.0017(17) 0.0019(17) C6 0.0141(19) 0.033(2) 0.028(2) 0.0068(19) 0.0010(17) 0.0020(17) C7 0.024(2) 0.032(2) 0.026(2) 0.0042(19) 0.0074(18) 0.0122(19) C8 0.030(2) 0.027(2) 0.026(2) -0.0017(19) -0.0039(18) 0.011(2) C9 0.022(2) 0.034(3) 0.038(3) 0.011(2) 0.000(2) -0.005(2) C10 0.033(3) 0.029(2) 0.055(3) 0.010(2) -0.006(2) -0.003(2) C11 0.026(2) 0.021(2) 0.037(3) 0.0091(19) -0.008(2) 0.0009(19) C12 0.034(3) 0.021(2) 0.033(3) 0.0010(19) -0.006(2) 0.010(2) C13 0.022(2) 0.041(3) 0.038(3) 0.013(2) 0.000(2) 0.009(2) C14 0.015(2) 0.031(3) 0.045(3) 0.012(2) -0.008(2) 0.0022(19) C15 0.033(3) 0.035(3) 0.036(3) 0.002(2) -0.015(2) 0.004(2) C16 0.033(3) 0.033(3) 0.029(3) 0.007(2) -0.002(2) 0.009(2) C17 0.017(2) 0.022(2) 0.023(2) 0.0025(17) 0.0049(16) 0.0006(17) C18 0.032(3) 0.029(2) 0.031(2) 0.003(2) 0.0077(19) 0.013(2) C19 0.033(3) 0.024(2) 0.029(2) 0.0011(19) 0.0057(19) 0.0070(19) C20 0.0176(17) 0.032(2) 0.035(2) -0.005(2) 0.0005(15) -0.002(2) C21 0.021(2) 0.044(3) 0.048(3) 0.007(3) -0.004(2) 0.003(2) C22 0.030(3) 0.032(3) 0.066(4) -0.020(3) 0.005(3) -0.009(2) C23 0.019(2) 0.050(4) 0.045(3) 0.006(2) 0.0071(19) 0.001(2) C24 0.021(2) 0.016(2) 0.028(2) 0.0012(18) 0.0003(18) -0.0031(17) C25 0.033(3) 0.026(2) 0.036(3) -0.004(2) 0.005(2) 0.001(2) C26 0.041(3) 0.018(2) 0.045(3) 0.006(2) -0.009(2) 0.000(2) C27 0.024(2) 0.029(2) 0.037(3) 0.000(2) -0.004(2) -0.007(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Pd1 N2 2.028(4) . ? Pd1 P 2.2671(11) . ? Pd1 Cl1 2.2981(12) . ? Pd1 Cl2 2.3705(14) . ? Cl3 C28 1.821(19) . ? Cl4 C28 1.814(19) . ? P C17 1.824(5) . ? P C24 1.855(5) . ? P C20 1.856(4) . ? N1 C17 1.356(6) . ? N1 C19 1.372(6) . ? N1 C4 1.447(6) . ? N2 C17 1.342(6) . ? N2 C18 1.363(6) . ? C1 C14 1.525(7) . ? C1 C2 1.566(7) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.531(6) . ? C2 H2A 0.99 . ? C2 H2B 0.99 . ? C3 C8 1.390(7) . ? C3 C4 1.394(6) . ? C4 C5 1.385(6) . ? C5 C6 1.408(7) . ? C5 H5 0.95 . ? C6 C7 1.397(7) . ? C6 C9 1.501(7) . ? C7 C8 1.378(7) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C9 C10 1.579(7) . ? C9 H9A 0.99 . ? C9 H9B 0.99 . ? C10 C11 1.516(7) . ? C10 H10A 0.99 . ? C10 H10B 0.99 . ? C11 C16 1.390(8) . ? C11 C12 1.409(8) . ? C12 C13 1.399(8) . ? C12 H12 0.95 . ? C13 C14 1.363(8) . ? C13 H13 0.95 . ? C14 C15 1.400(9) . ? C15 C16 1.387(8) . ? C15 H15 0.95 . ? C16 H16 0.95 . ? C18 C19 1.362(7) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C23 1.531(7) . ? C20 C21 1.536(8) . ? C20 C22 1.539(7) . ? C21 H21A 0.98 . ? C21 H21B 0.98 . ? C21 H21C 0.98 . ? C22 H22A 0.98 . ? C22 H22B 0.98 . ? C22 H22C 0.98 . ? C23 H23A 0.98 . ? C23 H23B 0.98 . ? C23 H23C 0.98 . ? C24 C27 1.512(6) . ? C24 C25 1.539(7) . ? C24 C26 1.540(6) . ? C25 H25A 0.98 . ? C25 H25B 0.98 . ? C25 H25C 0.98 . ? C26 H26A 0.98 . ? C26 H26B 0.98 . ? C26 H26C 0.98 . ? C27 H27A 0.98 . ? C27 H27B 0.98 . ? C27 H27C 0.98 . ? C28 H28A 0.99 . ? C28 H28B 0.99 . ? 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 Pd1 P 70.68(11) . . ? N2 Pd1 Cl1 170.26(11) . . ? P Pd1 Cl1 99.96(5) . . ? N2 Pd1 Cl2 95.64(11) . . ? P Pd1 Cl2 166.19(5) . . ? Cl1 Pd1 Cl2 93.79(5) . . ? C17 P C24 111.7(2) . . ? C17 P C20 107.8(2) . . ? C24 P C20 117.4(2) . . ? C17 P Pd1 81.86(14) . . ? C24 P Pd1 114.87(15) . . ? C20 P Pd1 117.10(15) . . ? C17 N1 C19 106.8(4) . . ? C17 N1 C4 127.0(4) . . ? C19 N1 C4 126.2(4) . . ? C17 N2 C18 108.9(4) . . ? C17 N2 Pd1 104.7(3) . . ? C18 N2 Pd1 144.8(3) . . ? C14 C1 C2 113.1(4) . . ? C14 C1 H1A 109 . . ? C2 C1 H1A 109 . . ? C14 C1 H1B 109 . . ? C2 C1 H1B 109 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 113.1(4) . . ? C3 C2 H2A 109 . . ? C1 C2 H2A 109 . . ? C3 C2 H2B 109 . . ? C1 C2 H2B 109 . . ? H2A C2 H2B 107.8 . . ? C8 C3 C4 115.7(4) . . ? C8 C3 C2 120.1(4) . . ? C4 C3 C2 122.7(4) . . ? C5 C4 C3 122.4(4) . . ? C5 C4 N1 117.1(4) . . ? C3 C4 N1 120.2(4) . . ? C4 C5 C6 119.5(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 116.2(4) . . ? C7 C6 C9 121.6(4) . . ? C5 C6 C9 121.1(4) . . ? C8 C7 C6 121.4(4) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C7 C8 C3 121.1(4) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? C6 C9 C10 112.9(4) . . ? C6 C9 H9A 109 . . ? C10 C9 H9A 109 . . ? C6 C9 H9B 109 . . ? C10 C9 H9B 109 . . ? H9A C9 H9B 107.8 . . ? C11 C10 C9 113.3(4) . . ? C11 C10 H10A 108.9 . . ? C9 C10 H10A 108.9 . . ? C11 C10 H10B 108.9 . . ? C9 C10 H10B 108.9 . . ? H10A C10 H10B 107.7 . . ? C16 C11 C12 117.0(5) . . ? C16 C11 C10 120.7(5) . . ? C12 C11 C10 121.4(5) . . ? C13 C12 C11 120.3(5) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C14 C13 C12 120.2(5) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 118.6(5) . . ? C13 C14 C1 121.9(5) . . ? C15 C14 C1 118.0(6) . . ? C16 C15 C14 120.3(6) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 120.3(5) . . ? C15 C16 H16 119.8 . . ? C11 C16 H16 119.8 . . ? N2 C17 N1 108.8(4) . . ? N2 C17 P 102.8(3) . . ? N1 C17 P 146.7(4) . . ? C19 C18 N2 106.7(4) . . ? C19 C18 H18 126.7 . . ? N2 C18 H18 126.7 . . ? C18 C19 N1 108.8(4) . . ? C18 C19 H19 125.6 . . ? N1 C19 H19 125.6 . . ? C23 C20 C21 110.8(4) . . ? C23 C20 C22 108.7(5) . . ? C21 C20 C22 109.6(4) . . ? C23 C20 P 114.2(3) . . ? C21 C20 P 108.2(4) . . ? C22 C20 P 105.1(3) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C27 C24 C25 110.0(4) . . ? C27 C24 C26 110.3(4) . . ? C25 C24 C26 109.9(4) . . ? C27 C24 P 105.7(3) . . ? C25 C24 P 113.8(3) . . ? C26 C24 P 107.0(3) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C24 C26 H26A 109.5 . . ? C24 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C24 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? Cl4 C28 Cl3 101.3(13) . . ? Cl4 C28 H28A 111.5 . . ? Cl3 C28 H28A 111.5 . . ? Cl4 C28 H28B 111.5 . . ? Cl3 C28 H28B 111.5 . . ? H28A C28 H28B 109.3 . . ? #===END