# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'P Braunstein' _publ_contact_author_email BRAUNST@CHIMIE.U-STRASBG.FR _publ_section_title ; Synthesis and characterization of Co and Ni complexes stabilized by keto- and acetamide-derived P,O-type phosphine ligands ; loop_ _publ_author_name 'P Braunstein' 'Magno Agostinho' 'Teresa Aviles' 'Vitor Rosa' 'Richard Welter' # Attachment 'Complex1.cif' data_Complex1 _database_code_depnum_ccdc_archive 'CCDC 698954' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H22 Co I2 O P' _chemical_formula_sum 'C25 H22 Co I2 O P' _chemical_formula_weight 682.13 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.2740(2) _cell_length_b 8.19200(10) _cell_length_c 28.0720(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.9260(8) _cell_angle_gamma 90.00 _cell_volume 2353.94(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5442 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.925 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 3.435 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean . _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11181 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0656 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 30.02 _reflns_number_total 6859 _reflns_number_gt 4838 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0057P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6859 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0688 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.002 _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 I1 I 0.188103(19) -0.09408(2) 0.041451(7) 0.02822(6) Uani 1 1 d . . . I2 I 0.509189(17) 0.10217(2) 0.088429(8) 0.03002(7) Uani 1 1 d . . . Co1 Co 0.28944(3) 0.19592(5) 0.046759(13) 0.02059(10) Uani 1 1 d . . . P1 P 0.22390(6) 0.25889(9) 0.11822(3) 0.01901(16) Uani 1 1 d . . . O1 O 0.2067(2) 0.1666(3) 0.23946(7) 0.0381(6) Uani 1 1 d . . . C1 C 0.2162(2) 0.0837(3) 0.15923(10) 0.0221(6) Uani 1 1 d . . . H1A H 0.1715 -0.0078 0.1415 0.027 Uiso 1 1 calc . . . H1B H 0.3064 0.0479 0.1693 0.027 Uiso 1 1 calc . . . C2 C 0.1464(3) 0.1174(3) 0.20351(10) 0.0241(6) Uani 1 1 d . . . C3 C 0.0023(3) 0.0897(3) 0.20182(10) 0.0229(6) Uani 1 1 d . . . C4 C -0.0662(3) -0.0117(4) 0.16881(11) 0.0300(7) Uani 1 1 d . . . H4 H -0.0212 -0.0646 0.1450 0.036 Uiso 1 1 calc . . . C5 C -0.1986(3) -0.0367(4) 0.17021(12) 0.0400(9) Uani 1 1 d . . . H5 H -0.2440 -0.1077 0.1478 0.048 Uiso 1 1 calc . . . C6 C -0.2648(3) 0.0416(5) 0.20433(13) 0.0430(9) Uani 1 1 d . . . H6 H -0.3561 0.0254 0.2052 0.052 Uiso 1 1 calc . . . C7 C -0.1990(3) 0.1429(4) 0.23701(12) 0.0427(9) Uani 1 1 d . . . H7 H -0.2453 0.1970 0.2603 0.051 Uiso 1 1 calc . . . C8 C -0.0660(3) 0.1670(4) 0.23642(11) 0.0342(8) Uani 1 1 d . . . H8 H -0.0211 0.2360 0.2595 0.041 Uiso 1 1 calc . . . C9 C 0.0609(2) 0.3462(3) 0.11668(10) 0.0208(6) Uani 1 1 d . . . C10 C -0.0358(3) 0.2864(4) 0.08307(10) 0.0242(6) Uani 1 1 d . . . H10 H -0.0135 0.2097 0.0597 0.029 Uiso 1 1 calc . . . C11 C -0.1639(3) 0.3385(4) 0.08368(11) 0.0297(7) Uani 1 1 d . . . H11 H -0.2291 0.2978 0.0607 0.036 Uiso 1 1 calc . . . C12 C -0.1971(3) 0.4496(4) 0.11764(11) 0.0320(7) Uani 1 1 d . . . H12 H -0.2853 0.4840 0.1181 0.038 Uiso 1 1 calc . . . C13 C -0.1030(3) 0.5105(4) 0.15074(11) 0.0329(8) Uani 1 1 d . . . H13 H -0.1261 0.5879 0.1738 0.039 Uiso 1 1 calc . . . C14 C 0.0267(3) 0.4587(4) 0.15055(11) 0.0276(7) Uani 1 1 d . . . H14 H 0.0915 0.5004 0.1736 0.033 Uiso 1 1 calc . . . C15 C 0.3314(2) 0.4068(3) 0.15004(10) 0.0204(6) Uani 1 1 d . . . C16 C 0.4245(3) 0.3616(3) 0.18698(11) 0.0258(7) Uani 1 1 d . . . H16 H 0.4261 0.2530 0.1989 0.031 Uiso 1 1 calc . . . C17 C 0.5143(3) 0.4749(4) 0.20627(11) 0.0312(7) Uani 1 1 d . . . H17 H 0.5766 0.4434 0.2316 0.037 Uiso 1 1 calc . . . C18 C 0.5146(3) 0.6317(4) 0.18937(12) 0.0325(8) Uani 1 1 d . . . H18 H 0.5777 0.7077 0.2024 0.039 Uiso 1 1 calc . . . C19 C 0.4224(3) 0.6789(4) 0.15320(12) 0.0322(8) Uani 1 1 d . . . H19 H 0.4219 0.7877 0.1415 0.039 Uiso 1 1 calc . . . C20 C 0.3305(3) 0.5670(4) 0.13392(11) 0.0280(7) Uani 1 1 d . . . H20 H 0.2665 0.6007 0.1095 0.034 Uiso 1 1 calc . . . C21 C 0.1683(3) 0.2887(4) -0.00991(11) 0.0289(7) Uani 1 1 d . . . H21 H 0.0783 0.2631 -0.0162 0.035 Uiso 1 1 calc . . . C22 C 0.2202(3) 0.4156(4) 0.01902(11) 0.0310(7) Uani 1 1 d . . . H22 H 0.1711 0.4933 0.0351 0.037 Uiso 1 1 calc . . . C23 C 0.3589(3) 0.4091(4) 0.02046(12) 0.0335(8) Uani 1 1 d . . . H23 H 0.4191 0.4781 0.0385 0.040 Uiso 1 1 calc . . . C24 C 0.3903(3) 0.2784(4) -0.01049(11) 0.0357(8) Uani 1 1 d . . . H24 H 0.4757 0.2476 -0.0176 0.043 Uiso 1 1 calc . . . C25 C 0.2744(3) 0.2044(4) -0.02838(10) 0.0323(7) Uani 1 1 d . . . H25 H 0.2671 0.1132 -0.0493 0.039 Uiso 1 1 calc . . . 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 I1 0.03389(12) 0.02086(11) 0.02889(12) -0.00230(9) -0.00326(9) -0.00391(8) I2 0.01795(10) 0.03590(14) 0.03628(13) -0.00272(10) 0.00266(8) 0.00245(8) Co1 0.02009(19) 0.0202(2) 0.0219(2) 0.00033(17) 0.00391(15) -0.00132(16) P1 0.0178(3) 0.0187(4) 0.0205(4) 0.0005(3) 0.0011(3) 0.0000(3) O1 0.0358(12) 0.0533(15) 0.0245(13) -0.0011(11) -0.0015(10) -0.0122(11) C1 0.0225(14) 0.0198(15) 0.0239(16) 0.0027(13) 0.0018(11) -0.0007(12) C2 0.0275(15) 0.0237(16) 0.0208(16) 0.0047(13) 0.0012(12) -0.0019(13) C3 0.0254(14) 0.0221(16) 0.0214(16) 0.0076(13) 0.0025(12) -0.0004(12) C4 0.0291(16) 0.0358(19) 0.0251(17) 0.0050(15) 0.0029(13) -0.0018(14) C5 0.0272(17) 0.050(2) 0.041(2) 0.0123(19) -0.0057(15) -0.0088(16) C6 0.0234(16) 0.062(3) 0.044(2) 0.024(2) 0.0052(15) 0.0009(17) C7 0.0351(18) 0.059(2) 0.037(2) 0.0115(19) 0.0173(16) 0.0140(18) C8 0.0374(18) 0.039(2) 0.0265(18) 0.0040(16) 0.0064(14) 0.0031(16) C9 0.0211(14) 0.0190(15) 0.0223(16) 0.0022(13) 0.0012(11) 0.0013(12) C10 0.0236(14) 0.0246(17) 0.0243(16) -0.0006(13) 0.0012(12) -0.0009(13) C11 0.0210(15) 0.0379(19) 0.0297(18) 0.0045(15) -0.0012(13) -0.0031(14) C12 0.0237(15) 0.0371(19) 0.036(2) 0.0039(16) 0.0073(13) 0.0109(15) C13 0.0323(17) 0.0327(19) 0.0345(19) -0.0039(15) 0.0076(14) 0.0110(15) C14 0.0252(15) 0.0285(17) 0.0286(18) -0.0011(14) -0.0003(12) 0.0021(13) C15 0.0188(13) 0.0186(15) 0.0240(16) -0.0037(12) 0.0030(11) -0.0020(11) C16 0.0280(15) 0.0204(15) 0.0287(18) -0.0020(13) 0.0000(13) -0.0001(13) C17 0.0238(15) 0.036(2) 0.0328(19) -0.0068(16) -0.0044(13) -0.0016(14) C18 0.0275(16) 0.0324(19) 0.038(2) -0.0097(16) 0.0041(14) -0.0105(14) C19 0.0353(18) 0.0203(17) 0.042(2) -0.0060(15) 0.0067(15) -0.0044(14) C20 0.0310(16) 0.0229(17) 0.0296(18) 0.0019(14) -0.0012(13) 0.0001(13) C21 0.0324(16) 0.0273(17) 0.0263(17) 0.0104(14) -0.0022(13) 0.0025(14) C22 0.0410(18) 0.0247(17) 0.0284(18) 0.0077(14) 0.0097(14) 0.0055(14) C23 0.0406(18) 0.0301(19) 0.0308(19) 0.0031(15) 0.0092(14) -0.0110(15) C24 0.0359(18) 0.041(2) 0.0322(19) 0.0076(16) 0.0163(14) -0.0025(16) C25 0.0465(19) 0.0320(19) 0.0189(16) 0.0043(14) 0.0059(14) -0.0033(16) _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 I1 Co1 2.5930(4) . ? I2 Co1 2.5694(4) . ? Co1 C23 2.048(3) . ? Co1 C22 2.063(3) . ? Co1 C21 2.078(3) . ? Co1 C24 2.098(3) . ? Co1 C25 2.103(3) . ? Co1 P1 2.2307(8) . ? P1 C9 1.818(3) . ? P1 C15 1.821(3) . ? P1 C1 1.846(3) . ? O1 C2 1.207(3) . ? C1 C2 1.513(4) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.494(4) . ? C3 C4 1.390(4) . ? C3 C8 1.398(4) . ? C4 C5 1.380(4) . ? C4 H4 0.9500 . ? C5 C6 1.380(5) . ? C5 H5 0.9500 . ? C6 C7 1.371(5) . ? C6 H6 0.9500 . ? C7 C8 1.382(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.391(4) . ? C9 C10 1.399(4) . ? C10 C11 1.385(4) . ? C10 H10 0.9500 . ? C11 C12 1.382(4) . ? C11 H11 0.9500 . ? C12 C13 1.376(4) . ? C12 H12 0.9500 . ? C13 C14 1.399(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C20 1.388(4) . ? C15 C16 1.399(4) . ? C16 C17 1.386(4) . ? C16 H16 0.9500 . ? C17 C18 1.369(4) . ? C17 H17 0.9500 . ? C18 C19 1.382(4) . ? C18 H18 0.9500 . ? C19 C20 1.391(4) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C21 C22 1.396(4) . ? C21 C25 1.425(4) . ? C21 H21 0.9500 . ? C22 C23 1.423(4) . ? C22 H22 0.9500 . ? C23 C24 1.433(4) . ? C23 H23 0.9500 . ? C24 C25 1.392(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? 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 C23 Co1 C22 40.51(12) . . ? C23 Co1 C21 67.45(12) . . ? C22 Co1 C21 39.42(12) . . ? C23 Co1 C24 40.42(12) . . ? C22 Co1 C24 66.84(12) . . ? C21 Co1 C24 66.32(12) . . ? C23 Co1 C25 66.94(12) . . ? C22 Co1 C25 66.38(12) . . ? C21 Co1 C25 39.85(11) . . ? C24 Co1 C25 38.70(12) . . ? C23 Co1 P1 105.58(9) . . ? C22 Co1 P1 90.97(9) . . ? C21 Co1 P1 113.37(8) . . ? C24 Co1 P1 145.26(10) . . ? C25 Co1 P1 153.19(9) . . ? C23 Co1 I2 95.69(9) . . ? C22 Co1 I2 133.91(9) . . ? C21 Co1 I2 154.56(8) . . ? C24 Co1 I2 88.42(9) . . ? C25 Co1 I2 116.92(9) . . ? P1 Co1 I2 88.91(2) . . ? C23 Co1 I1 155.66(9) . . ? C22 Co1 I1 130.83(9) . . ? C21 Co1 I1 94.59(8) . . ? C24 Co1 I1 118.26(10) . . ? C25 Co1 I1 88.73(9) . . ? P1 Co1 I1 96.48(2) . . ? I2 Co1 I1 94.882(14) . . ? C9 P1 C15 105.56(12) . . ? C9 P1 C1 103.42(12) . . ? C15 P1 C1 105.57(13) . . ? C9 P1 Co1 114.72(10) . . ? C15 P1 Co1 112.20(9) . . ? C1 P1 Co1 114.42(9) . . ? C2 C1 P1 114.76(19) . . ? C2 C1 H1A 108.6 . . ? P1 C1 H1A 108.6 . . ? C2 C1 H1B 108.6 . . ? P1 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? O1 C2 C3 120.9(3) . . ? O1 C2 C1 120.1(3) . . ? C3 C2 C1 119.0(2) . . ? C4 C3 C8 118.6(3) . . ? C4 C3 C2 123.7(3) . . ? C8 C3 C2 117.7(3) . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C6 C7 C8 120.6(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C7 C8 C3 120.0(3) . . ? C7 C8 H8 120.0 . . ? C3 C8 H8 120.0 . . ? C14 C9 C10 119.2(2) . . ? C14 C9 P1 122.0(2) . . ? C10 C9 P1 118.5(2) . . ? C11 C10 C9 120.3(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C12 C11 C10 120.2(3) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 120.3(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 120.1(3) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C9 C14 C13 120.0(3) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C20 C15 C16 118.5(3) . . ? C20 C15 P1 118.9(2) . . ? C16 C15 P1 122.3(2) . . ? C17 C16 C15 120.1(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.9(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 119.7(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C15 C20 C19 120.7(3) . . ? C15 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C22 C21 C25 107.9(3) . . ? C22 C21 Co1 69.72(18) . . ? C25 C21 Co1 71.04(16) . . ? C22 C21 H21 126.1 . . ? C25 C21 H21 126.1 . . ? Co1 C21 H21 124.8 . . ? C21 C22 C23 108.7(3) . . ? C21 C22 Co1 70.86(17) . . ? C23 C22 Co1 69.20(17) . . ? C21 C22 H22 125.7 . . ? C23 C22 H22 125.7 . . ? Co1 C22 H22 125.9 . . ? C22 C23 C24 106.7(3) . . ? C22 C23 Co1 70.30(16) . . ? C24 C23 Co1 71.65(17) . . ? C22 C23 H23 126.6 . . ? C24 C23 H23 126.6 . . ? Co1 C23 H23 123.1 . . ? C25 C24 C23 108.3(3) . . ? C25 C24 Co1 70.86(17) . . ? C23 C24 Co1 67.93(16) . . ? C25 C24 H24 125.8 . . ? C23 C24 H24 125.8 . . ? Co1 C24 H24 126.9 . . ? C24 C25 C21 108.4(3) . . ? C24 C25 Co1 70.45(18) . . ? C21 C25 Co1 69.12(16) . . ? C24 C25 H25 125.8 . . ? C21 C25 H25 125.8 . . ? Co1 C25 H25 126.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C23 Co1 P1 C9 82.95(14) . . . . ? C22 Co1 P1 C9 44.64(14) . . . . ? C21 Co1 P1 C9 11.20(14) . . . . ? C24 Co1 P1 C9 92.89(19) . . . . ? C25 Co1 P1 C9 13.4(2) . . . . ? I2 Co1 P1 C9 178.55(10) . . . . ? I1 Co1 P1 C9 -86.66(10) . . . . ? C23 Co1 P1 C15 -37.50(14) . . . . ? C22 Co1 P1 C15 -75.81(13) . . . . ? C21 Co1 P1 C15 -109.25(13) . . . . ? C24 Co1 P1 C15 -27.56(19) . . . . ? C25 Co1 P1 C15 -107.0(2) . . . . ? I2 Co1 P1 C15 58.10(10) . . . . ? I1 Co1 P1 C15 152.89(10) . . . . ? C23 Co1 P1 C1 -157.74(13) . . . . ? C22 Co1 P1 C1 163.95(13) . . . . ? C21 Co1 P1 C1 130.51(13) . . . . ? C24 Co1 P1 C1 -147.80(19) . . . . ? C25 Co1 P1 C1 132.7(2) . . . . ? I2 Co1 P1 C1 -62.14(9) . . . . ? I1 Co1 P1 C1 32.65(9) . . . . ? C9 P1 C1 C2 -42.6(2) . . . . ? C15 P1 C1 C2 68.1(2) . . . . ? Co1 P1 C1 C2 -168.07(17) . . . . ? P1 C1 C2 O1 -90.4(3) . . . . ? P1 C1 C2 C3 89.3(3) . . . . ? O1 C2 C3 C4 -158.9(3) . . . . ? C1 C2 C3 C4 21.4(4) . . . . ? O1 C2 C3 C8 19.2(4) . . . . ? C1 C2 C3 C8 -160.5(3) . . . . ? C8 C3 C4 C5 -0.4(5) . . . . ? C2 C3 C4 C5 177.7(3) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C4 C5 C6 C7 -0.6(5) . . . . ? C5 C6 C7 C8 -0.4(5) . . . . ? C6 C7 C8 C3 1.0(5) . . . . ? C4 C3 C8 C7 -0.6(4) . . . . ? C2 C3 C8 C7 -178.8(3) . . . . ? C15 P1 C9 C14 -24.9(3) . . . . ? C1 P1 C9 C14 85.8(3) . . . . ? Co1 P1 C9 C14 -148.9(2) . . . . ? C15 P1 C9 C10 161.3(2) . . . . ? C1 P1 C9 C10 -88.1(2) . . . . ? Co1 P1 C9 C10 37.2(2) . . . . ? C14 C9 C10 C11 -0.2(4) . . . . ? P1 C9 C10 C11 173.9(2) . . . . ? C9 C10 C11 C12 -0.2(4) . . . . ? C10 C11 C12 C13 0.7(5) . . . . ? C11 C12 C13 C14 -0.8(5) . . . . ? C10 C9 C14 C13 0.1(4) . . . . ? P1 C9 C14 C13 -173.7(2) . . . . ? C12 C13 C14 C9 0.4(5) . . . . ? C9 P1 C15 C20 -54.6(2) . . . . ? C1 P1 C15 C20 -163.7(2) . . . . ? Co1 P1 C15 C20 71.1(2) . . . . ? C9 P1 C15 C16 132.3(2) . . . . ? C1 P1 C15 C16 23.2(3) . . . . ? Co1 P1 C15 C16 -102.0(2) . . . . ? C20 C15 C16 C17 -0.8(4) . . . . ? P1 C15 C16 C17 172.3(2) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? C16 C17 C18 C19 1.3(5) . . . . ? C17 C18 C19 C20 -0.4(5) . . . . ? C16 C15 C20 C19 1.7(4) . . . . ? P1 C15 C20 C19 -171.7(2) . . . . ? C18 C19 C20 C15 -1.1(5) . . . . ? C23 Co1 C21 C22 -37.68(17) . . . . ? C24 Co1 C21 C22 -81.79(19) . . . . ? C25 Co1 C21 C22 -118.2(3) . . . . ? P1 Co1 C21 C22 60.21(18) . . . . ? I2 Co1 C21 C22 -89.2(2) . . . . ? I1 Co1 C21 C22 159.30(16) . . . . ? C23 Co1 C21 C25 80.53(19) . . . . ? C22 Co1 C21 C25 118.2(3) . . . . ? C24 Co1 C21 C25 36.43(18) . . . . ? P1 Co1 C21 C25 178.42(15) . . . . ? I2 Co1 C21 C25 29.1(3) . . . . ? I1 Co1 C21 C25 -82.49(17) . . . . ? C25 C21 C22 C23 -2.1(3) . . . . ? Co1 C21 C22 C23 59.1(2) . . . . ? C25 C21 C22 Co1 -61.1(2) . . . . ? C23 Co1 C22 C21 119.6(3) . . . . ? C24 Co1 C22 C21 80.36(19) . . . . ? C25 Co1 C22 C21 38.04(17) . . . . ? P1 Co1 C22 C21 -127.18(16) . . . . ? I2 Co1 C22 C21 143.40(14) . . . . ? I1 Co1 C22 C21 -27.8(2) . . . . ? C21 Co1 C22 C23 -119.6(3) . . . . ? C24 Co1 C22 C23 -39.27(18) . . . . ? C25 Co1 C22 C23 -81.59(19) . . . . ? P1 Co1 C22 C23 113.19(18) . . . . ? I2 Co1 C22 C23 23.8(2) . . . . ? I1 Co1 C22 C23 -147.39(16) . . . . ? C21 C22 C23 C24 2.7(3) . . . . ? Co1 C22 C23 C24 62.8(2) . . . . ? C21 C22 C23 Co1 -60.1(2) . . . . ? C21 Co1 C23 C22 36.70(18) . . . . ? C24 Co1 C23 C22 116.1(3) . . . . ? C25 Co1 C23 C22 80.1(2) . . . . ? P1 Co1 C23 C22 -72.58(18) . . . . ? I2 Co1 C23 C22 -163.04(17) . . . . ? I1 Co1 C23 C22 81.6(3) . . . . ? C22 Co1 C23 C24 -116.1(3) . . . . ? C21 Co1 C23 C24 -79.4(2) . . . . ? C25 Co1 C23 C24 -36.06(19) . . . . ? P1 Co1 C23 C24 171.27(16) . . . . ? I2 Co1 C23 C24 80.81(18) . . . . ? I1 Co1 C23 C24 -34.5(3) . . . . ? C22 C23 C24 C25 -2.4(4) . . . . ? Co1 C23 C24 C25 59.5(2) . . . . ? C22 C23 C24 Co1 -61.9(2) . . . . ? C23 Co1 C24 C25 -120.0(3) . . . . ? C22 Co1 C24 C25 -80.6(2) . . . . ? C21 Co1 C24 C25 -37.48(19) . . . . ? P1 Co1 C24 C25 -134.83(18) . . . . ? I2 Co1 C24 C25 139.36(19) . . . . ? I1 Co1 C24 C25 44.7(2) . . . . ? C22 Co1 C24 C23 39.36(19) . . . . ? C21 Co1 C24 C23 82.5(2) . . . . ? C25 Co1 C24 C23 120.0(3) . . . . ? P1 Co1 C24 C23 -14.9(3) . . . . ? I2 Co1 C24 C23 -100.68(18) . . . . ? I1 Co1 C24 C23 164.63(16) . . . . ? C23 C24 C25 C21 1.2(4) . . . . ? Co1 C24 C25 C21 58.9(2) . . . . ? C23 C24 C25 Co1 -57.7(2) . . . . ? C22 C21 C25 C24 0.5(4) . . . . ? Co1 C21 C25 C24 -59.7(2) . . . . ? C22 C21 C25 Co1 60.3(2) . . . . ? C23 Co1 C25 C24 37.6(2) . . . . ? C22 Co1 C25 C24 81.9(2) . . . . ? C21 Co1 C25 C24 119.6(3) . . . . ? P1 Co1 C25 C24 116.4(2) . . . . ? I2 Co1 C25 C24 -46.9(2) . . . . ? I1 Co1 C25 C24 -141.73(19) . . . . ? C23 Co1 C25 C21 -81.9(2) . . . . ? C22 Co1 C25 C21 -37.64(18) . . . . ? C24 Co1 C25 C21 -119.6(3) . . . . ? P1 Co1 C25 C21 -3.2(3) . . . . ? I2 Co1 C25 C21 -166.46(15) . . . . ? I1 Co1 C25 C21 98.70(17) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.846 _refine_diff_density_min -0.925 _refine_diff_density_rms 0.142 # Attachment 'Complex_3_new.cif' data_complex_5 _database_code_depnum_ccdc_archive 'CCDC 698955' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C19 H18 Co I2 N O P), 3/2(C H2 Cl2)' _chemical_formula_sum 'C39.50 H39 Cl3 Co2 I4 N2 O2 P2' _chemical_formula_weight 1367.48 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0520(3) _cell_length_b 15.4070(5) _cell_length_c 19.8740(7) _cell_angle_alpha 89.393(2) _cell_angle_beta 82.027(2) _cell_angle_gamma 76.3740(14) _cell_volume 2372.33(14) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7323 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1306 _exptl_absorpt_coefficient_mu 3.573 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19144 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0957 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 30.07 _reflns_number_total 13854 _reflns_number_gt 8377 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1161P)^2^+6.7228P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13854 _refine_ls_number_parameters 506 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1971 _refine_ls_wR_factor_gt 0.1627 _refine_ls_goodness_of_fit_ref 0.912 _refine_ls_restrained_S_all 0.912 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.40822(7) -0.44758(4) 0.65978(3) 0.04526(16) Uani 1 1 d . . . I2 I 0.40257(6) -0.27170(3) 0.52664(3) 0.03691(14) Uani 1 1 d . . . I3 I 1.13886(6) 0.36670(3) 0.70510(3) 0.03519(13) Uani 1 1 d . . . I4 I 0.86428(6) 0.24649(3) 0.61783(3) 0.03439(13) Uani 1 1 d . . . Co1 Co 0.63349(11) -0.37836(6) 0.58540(5) 0.0254(2) Uani 1 1 d . . . Co2 Co 1.12214(11) 0.20430(6) 0.68601(5) 0.0271(2) Uani 1 1 d . . . P1 P 0.6269(2) -0.27534(11) 0.66206(10) 0.0256(4) Uani 1 1 d . . . P2 P 0.9632(2) 0.20835(12) 0.78585(10) 0.0268(4) Uani 1 1 d . . . O1 O 0.4468(6) -0.1132(3) 0.7604(3) 0.0349(12) Uani 1 1 d . . . O2 O 0.6587(7) 0.2769(4) 0.8988(3) 0.0433(13) Uani 1 1 d . . . N1 N 0.4181(7) -0.2300(4) 0.6967(3) 0.0297(13) Uani 1 1 d . . . N2 N 0.7849(7) 0.2945(4) 0.7903(3) 0.0312(13) Uani 1 1 d . . . C1 C 0.3567(8) -0.1589(4) 0.7407(4) 0.0296(15) Uani 1 1 d . . . C2 C 0.1648(9) -0.1400(6) 0.7629(5) 0.043(2) Uani 1 1 d . . . H2A H 0.1293 -0.0879 0.7940 0.065 Uiso 1 1 calc . . . H2B H 0.1358 -0.1920 0.7862 0.065 Uiso 1 1 calc . . . H2C H 0.1045 -0.1279 0.7230 0.065 Uiso 1 1 calc . . . C3 C 0.7080(8) -0.1801(4) 0.6272(4) 0.0274(14) Uani 1 1 d . . . C4 C 0.5974(8) -0.1061(5) 0.6062(4) 0.0318(16) Uani 1 1 d . . . H4 H 0.4770 -0.1027 0.6117 0.038 Uiso 1 1 calc . . . C5 C 0.6609(9) -0.0359(5) 0.5769(4) 0.0357(17) Uani 1 1 d . . . H5 H 0.5839 0.0150 0.5622 0.043 Uiso 1 1 calc . . . C6 C 0.8375(11) -0.0403(5) 0.5691(5) 0.043(2) Uani 1 1 d . . . H6 H 0.8803 0.0085 0.5504 0.051 Uiso 1 1 calc . . . C7 C 0.9499(10) -0.1153(6) 0.5885(5) 0.044(2) Uani 1 1 d . . . H7 H 1.0705 -0.1188 0.5817 0.053 Uiso 1 1 calc . . . C8 C 0.8878(8) -0.1866(5) 0.6180(4) 0.0327(16) Uani 1 1 d . . . H8 H 0.9650 -0.2383 0.6316 0.039 Uiso 1 1 calc . . . C9 C 0.7387(9) -0.3115(5) 0.7348(4) 0.0294(14) Uani 1 1 d . . . C10 C 0.7893(10) -0.2495(5) 0.7748(4) 0.0372(17) Uani 1 1 d . . . H10 H 0.7692 -0.1885 0.7626 0.045 Uiso 1 1 calc . . . C11 C 0.8675(11) -0.2768(6) 0.8313(5) 0.044(2) Uani 1 1 d . . . H11 H 0.8991 -0.2345 0.8584 0.052 Uiso 1 1 calc . . . C12 C 0.9004(14) -0.3665(8) 0.8487(5) 0.061(3) Uani 1 1 d . . . H12 H 0.9575 -0.3864 0.8868 0.073 Uiso 1 1 calc . . . C13 C 0.8477(15) -0.4266(7) 0.8090(5) 0.063(3) Uani 1 1 d . . . H13 H 0.8662 -0.4874 0.8216 0.076 Uiso 1 1 calc . . . C14 C 0.7703(13) -0.4008(5) 0.7526(5) 0.048(2) Uani 1 1 d . . . H14 H 0.7385 -0.4434 0.7259 0.058 Uiso 1 1 calc . . . C15 C 0.8503(10) -0.3757(5) 0.5183(5) 0.0412(19) Uani 1 1 d . . . H15 H 0.8786 -0.3222 0.5016 0.049 Uiso 1 1 calc . . . C16 C 0.8981(9) -0.4199(6) 0.5778(5) 0.0405(19) Uani 1 1 d . . . H16 H 0.9679 -0.4025 0.6075 0.049 Uiso 1 1 calc . . . C17 C 0.8246(10) -0.4936(5) 0.5854(4) 0.0388(18) Uani 1 1 d . . . H17 H 0.8326 -0.5339 0.6219 0.047 Uiso 1 1 calc . . . C18 C 0.7360(10) -0.4977(5) 0.5291(4) 0.0362(17) Uani 1 1 d . . . H18 H 0.6760 -0.5420 0.5211 0.043 Uiso 1 1 calc . . . C19 C 0.7519(10) -0.4263(6) 0.4876(4) 0.0388(18) Uani 1 1 d . . . H19 H 0.7055 -0.4133 0.4462 0.047 Uiso 1 1 calc . . . C20 C 0.6497(9) 0.3145(5) 0.8445(4) 0.0335(16) Uani 1 1 d . . . C21 C 0.4984(11) 0.3856(7) 0.8296(5) 0.057(3) Uani 1 1 d . . . H21A H 0.4072 0.3942 0.8687 0.085 Uiso 1 1 calc . . . H21B H 0.4546 0.3676 0.7896 0.085 Uiso 1 1 calc . . . H21C H 0.5342 0.4417 0.8206 0.085 Uiso 1 1 calc . . . C22 C 1.0733(10) 0.2264(6) 0.8566(4) 0.0371(17) Uani 1 1 d . . . C23 C 1.0369(11) 0.3069(6) 0.8903(5) 0.045(2) Uani 1 1 d . . . H23 H 0.9467 0.3540 0.8786 0.054 Uiso 1 1 calc . . . C24 C 1.1296(13) 0.3209(7) 0.9413(5) 0.057(3) Uani 1 1 d . . . H24 H 1.0999 0.3769 0.9649 0.068 Uiso 1 1 calc . . . C25 C 1.2619(12) 0.2560(9) 0.9579(5) 0.064(3) Uani 1 1 d . . . H25 H 1.3283 0.2674 0.9913 0.077 Uiso 1 1 calc . . . C26 C 1.2979(13) 0.1765(8) 0.9273(6) 0.063(3) Uani 1 1 d . . . H26 H 1.3881 0.1308 0.9407 0.075 Uiso 1 1 calc . . . C27 C 1.2069(11) 0.1568(7) 0.8751(5) 0.052(2) Uani 1 1 d . . . H27 H 1.2346 0.0993 0.8537 0.062 Uiso 1 1 calc . . . C28 C 0.8737(9) 0.1109(5) 0.8067(4) 0.0309(15) Uani 1 1 d . . . C29 C 0.8591(12) 0.0774(6) 0.8721(4) 0.0439(19) Uani 1 1 d . . . H29 H 0.9030 0.1025 0.9073 0.053 Uiso 1 1 calc . . . C30 C 0.7799(13) 0.0070(6) 0.8854(5) 0.050(2) Uani 1 1 d . . . H30 H 0.7761 -0.0188 0.9290 0.060 Uiso 1 1 calc . . . C31 C 0.7062(11) -0.0256(6) 0.8348(5) 0.048(2) Uani 1 1 d . . . H31 H 0.6438 -0.0704 0.8451 0.058 Uiso 1 1 calc . . . C32 C 0.7227(9) 0.0059(5) 0.7711(5) 0.0401(19) Uani 1 1 d . . . H32 H 0.6760 -0.0186 0.7365 0.048 Uiso 1 1 calc . . . C33 C 0.8079(9) 0.0740(5) 0.7560(4) 0.0373(17) Uani 1 1 d . . . H33 H 0.8209 0.0952 0.7110 0.045 Uiso 1 1 calc . . . C34 C 1.3712(9) 0.1428(6) 0.7017(5) 0.042(2) Uani 1 1 d . . . H34 H 1.4260 0.1575 0.7380 0.051 Uiso 1 1 calc . . . C35 C 1.2664(9) 0.0782(5) 0.7034(4) 0.0395(19) Uani 1 1 d . . . H35 H 1.2411 0.0420 0.7406 0.047 Uiso 1 1 calc . . . C36 C 1.2092(11) 0.0793(5) 0.6399(5) 0.048(2) Uani 1 1 d . . . H36 H 1.1361 0.0443 0.6266 0.058 Uiso 1 1 calc . . . C37 C 1.2803(11) 0.1426(6) 0.5980(5) 0.047(2) Uani 1 1 d . . . H37 H 1.2631 0.1559 0.5523 0.057 Uiso 1 1 calc . . . C38 C 1.3777(10) 0.1806(6) 0.6359(5) 0.044(2) Uani 1 1 d . . . H38 H 1.4388 0.2245 0.6206 0.053 Uiso 1 1 calc . . . C40 C 0.5384(10) 0.4389(12) 1.0178(18) 0.20(3) Uani 0.50 1 d PD . . H40A H 0.5678 0.4246 1.0640 0.244 Uiso 0.50 1 calc P . . H40B H 0.5536 0.3821 0.9922 0.244 Uiso 0.50 1 calc P . . Cl4 Cl 0.6692(9) 0.5010(5) 0.9776(4) 0.199(4) Uani 1 1 d D . . C39 C 0.6927(5) 0.2033(5) 1.0479(5) 0.200(14) Uani 1 1 d D . . H39A H 0.6652 0.2295 1.0039 0.240 Uiso 1 1 calc . . . H39B H 0.8197 0.1889 1.0463 0.240 Uiso 1 1 calc . . . Cl1 Cl 0.9118(4) 0.1793(4) 1.04027(19) 0.137(2) Uani 1 1 d D . . Cl2 Cl 0.6223(12) 0.1077(7) 1.0584(3) 0.149(5) Uani 0.50 1 d PD . . Cl3 Cl 0.6018(12) 0.2801(6) 1.1113(3) 0.160(5) Uani 0.50 1 d PD . . 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 I1 0.0571(3) 0.0435(3) 0.0422(3) -0.0019(2) 0.0029(2) -0.0315(3) I2 0.0338(2) 0.0386(3) 0.0370(3) -0.0030(2) -0.0129(2) -0.00114(19) I3 0.0415(3) 0.0301(2) 0.0389(3) 0.0064(2) -0.0085(2) -0.01681(19) I4 0.0349(2) 0.0386(3) 0.0331(3) 0.0058(2) -0.01204(19) -0.01149(19) Co1 0.0268(4) 0.0227(4) 0.0265(5) -0.0012(4) -0.0030(3) -0.0059(3) Co2 0.0253(4) 0.0256(5) 0.0306(5) 0.0027(4) -0.0046(4) -0.0060(3) P1 0.0237(8) 0.0248(8) 0.0288(10) -0.0014(7) -0.0023(6) -0.0075(6) P2 0.0275(8) 0.0258(8) 0.0294(10) 0.0028(7) -0.0066(7) -0.0096(7) O1 0.031(2) 0.032(3) 0.043(3) -0.008(2) -0.003(2) -0.011(2) O2 0.043(3) 0.050(3) 0.034(3) 0.005(3) 0.001(2) -0.008(3) N1 0.030(3) 0.029(3) 0.030(3) -0.003(3) 0.000(2) -0.009(2) N2 0.029(3) 0.031(3) 0.036(4) 0.002(3) -0.005(2) -0.010(2) C1 0.029(3) 0.023(3) 0.034(4) 0.008(3) -0.002(3) -0.002(3) C2 0.028(4) 0.043(4) 0.056(6) -0.011(4) 0.005(3) -0.008(3) C3 0.025(3) 0.024(3) 0.033(4) -0.011(3) 0.003(3) -0.011(2) C4 0.024(3) 0.029(4) 0.041(5) 0.001(3) 0.000(3) -0.007(3) C5 0.038(4) 0.027(3) 0.035(4) -0.003(3) 0.008(3) -0.002(3) C6 0.051(5) 0.026(4) 0.048(5) 0.003(3) 0.009(4) -0.012(3) C7 0.039(4) 0.045(5) 0.049(5) -0.007(4) 0.006(4) -0.020(4) C8 0.025(3) 0.030(4) 0.041(5) -0.005(3) 0.002(3) -0.008(3) C9 0.036(4) 0.026(3) 0.024(4) -0.001(3) -0.006(3) -0.004(3) C10 0.039(4) 0.043(4) 0.032(4) 0.003(3) -0.009(3) -0.013(3) C11 0.054(5) 0.040(4) 0.043(5) -0.005(4) -0.021(4) -0.015(4) C12 0.070(6) 0.073(7) 0.042(6) -0.001(5) -0.025(5) -0.009(5) C13 0.096(8) 0.041(5) 0.041(6) 0.007(4) -0.007(5) 0.004(5) C14 0.084(6) 0.030(4) 0.032(5) 0.002(3) -0.015(4) -0.013(4) C15 0.038(4) 0.030(4) 0.048(5) -0.006(4) 0.018(3) -0.007(3) C16 0.024(3) 0.044(4) 0.050(5) -0.017(4) -0.003(3) -0.002(3) C17 0.038(4) 0.028(4) 0.045(5) 0.005(3) -0.007(3) 0.002(3) C18 0.041(4) 0.021(3) 0.044(5) -0.014(3) -0.003(3) -0.002(3) C19 0.034(4) 0.048(5) 0.028(4) -0.004(3) -0.002(3) 0.002(3) C20 0.030(3) 0.037(4) 0.034(4) 0.002(3) -0.003(3) -0.009(3) C21 0.037(4) 0.071(6) 0.052(6) 0.007(5) 0.002(4) 0.001(4) C22 0.036(4) 0.052(5) 0.030(4) 0.008(4) -0.013(3) -0.020(3) C23 0.048(5) 0.043(5) 0.050(6) 0.002(4) -0.011(4) -0.024(4) C24 0.059(6) 0.075(7) 0.050(6) -0.002(5) -0.012(5) -0.039(5) C25 0.045(5) 0.104(9) 0.054(6) -0.007(6) -0.012(4) -0.036(6) C26 0.050(5) 0.086(8) 0.049(6) -0.003(6) -0.014(4) -0.004(5) C27 0.045(5) 0.068(6) 0.039(5) -0.002(4) -0.014(4) -0.002(4) C28 0.031(3) 0.029(3) 0.035(4) 0.006(3) -0.005(3) -0.012(3) C29 0.063(5) 0.045(5) 0.032(4) 0.004(4) -0.009(4) -0.028(4) C30 0.086(7) 0.037(5) 0.033(5) 0.007(4) 0.000(4) -0.030(4) C31 0.050(5) 0.036(4) 0.059(6) -0.003(4) 0.012(4) -0.024(4) C32 0.029(4) 0.034(4) 0.059(6) -0.003(4) -0.006(3) -0.010(3) C33 0.030(4) 0.037(4) 0.046(5) 0.005(4) -0.011(3) -0.008(3) C34 0.021(3) 0.047(5) 0.057(6) 0.007(4) -0.010(3) -0.001(3) C35 0.033(4) 0.032(4) 0.045(5) 0.019(4) -0.002(3) 0.007(3) C36 0.046(5) 0.032(4) 0.058(6) -0.017(4) -0.005(4) 0.007(3) C37 0.043(4) 0.053(5) 0.035(5) 0.003(4) 0.004(3) 0.004(4) C38 0.030(4) 0.038(4) 0.054(6) -0.001(4) 0.010(3) 0.001(3) C40 0.22(5) 0.23(5) 0.16(4) -0.11(4) 0.08(4) -0.10(5) Cl4 0.221(7) 0.176(6) 0.209(7) -0.116(5) 0.083(6) -0.124(5) C39 0.079(9) 0.43(4) 0.058(9) 0.119(16) -0.020(7) 0.017(15) Cl1 0.075(2) 0.292(7) 0.061(2) -0.034(3) -0.0002(17) -0.084(3) Cl2 0.187(8) 0.314(13) 0.019(2) 0.015(4) -0.001(3) -0.215(10) Cl3 0.154(7) 0.162(8) 0.076(5) 0.082(5) 0.049(5) 0.095(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 I1 Co1 2.5975(10) . ? I2 Co1 2.5775(10) . ? I3 Co2 2.5722(10) . ? I4 Co2 2.5876(10) . ? Co1 C15 2.053(7) . ? Co1 C17 2.057(7) . ? Co1 C16 2.059(7) . ? Co1 C18 2.095(7) . ? Co1 C19 2.101(8) . ? Co1 P1 2.198(2) . ? Co2 C36 2.065(8) . ? Co2 C35 2.068(7) . ? Co2 C34 2.071(7) . ? Co2 C37 2.105(9) . ? Co2 C38 2.108(7) . ? Co2 P2 2.200(2) . ? P1 N1 1.710(6) . ? P1 C9 1.821(7) . ? P1 C3 1.835(7) . ? P2 N2 1.703(6) . ? P2 C22 1.819(8) . ? P2 C28 1.833(7) . ? O1 C1 1.224(9) . ? O2 C20 1.222(9) . ? N1 C1 1.362(9) . ? N2 C20 1.401(9) . ? C1 C2 1.506(10) . ? C2 H2A 0.9801 . ? C2 H2B 0.9799 . ? C2 H2C 0.9800 . ? C3 C4 1.371(10) . ? C3 C8 1.413(9) . ? C4 C5 1.390(10) . ? C4 H4 0.9500 . ? C5 C6 1.395(11) . ? C5 H5 0.9499 . ? C6 C7 1.378(12) . ? C6 H6 0.9500 . ? C7 C8 1.402(11) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C14 1.391(11) . ? C9 C10 1.415(10) . ? C10 C11 1.377(11) . ? C10 H10 0.9500 . ? C11 C12 1.394(14) . ? C11 H11 0.9500 . ? C12 C13 1.398(15) . ? C12 H12 0.9498 . ? C13 C14 1.368(13) . ? C13 H13 0.9499 . ? C14 H14 0.9501 . ? C15 C16 1.413(13) . ? C15 C19 1.429(12) . ? C15 H15 0.9499 . ? C16 C17 1.396(11) . ? C16 H16 0.9497 . ? C17 C18 1.418(12) . ? C17 H17 0.9500 . ? C18 C19 1.387(11) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.496(12) . ? C21 H21A 0.9800 . ? C21 H21B 0.9799 . ? C21 H21C 0.9801 . ? C22 C23 1.365(12) . ? C22 C27 1.414(12) . ? C23 C24 1.386(13) . ? C23 H23 0.9500 . ? C24 C25 1.354(15) . ? C24 H24 0.9499 . ? C25 C26 1.324(16) . ? C25 H25 0.9499 . ? C26 C27 1.424(14) . ? C26 H26 0.9500 . ? C27 H27 0.9498 . ? C28 C33 1.386(11) . ? C28 C29 1.393(11) . ? C29 C30 1.388(11) . ? C29 H29 0.9502 . ? C30 C31 1.390(13) . ? C30 H30 0.9500 . ? C31 C32 1.352(13) . ? C31 H31 0.9500 . ? C32 C33 1.392(11) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? C34 C38 1.424(13) . ? C34 C35 1.446(12) . ? C34 H34 0.9498 . ? C35 C36 1.402(13) . ? C35 H35 0.9499 . ? C36 C37 1.444(13) . ? C36 H36 0.9500 . ? C37 C38 1.384(13) . ? C37 H37 0.9501 . ? C38 H38 0.9500 . ? C40 Cl4 1.7001(11) . ? C40 Cl4 1.7001(10) 2_667 ? C40 H40A 0.9826 . ? C40 H40B 0.9949 . ? Cl4 C40 1.7001(10) 2_667 ? C39 Cl2 1.6998(10) . ? C39 Cl3 1.6999(10) . ? C39 H39A 0.9901 . ? C39 H39B 0.9900 . ? 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 C15 Co1 C17 67.2(3) . . ? C15 Co1 C16 40.2(4) . . ? C17 Co1 C16 39.7(3) . . ? C15 Co1 C18 66.5(3) . . ? C17 Co1 C18 39.9(3) . . ? C16 Co1 C18 66.5(3) . . ? C15 Co1 C19 40.2(3) . . ? C17 Co1 C19 66.4(3) . . ? C16 Co1 C19 66.8(3) . . ? C18 Co1 C19 38.6(3) . . ? C15 Co1 P1 103.5(2) . . ? C17 Co1 P1 116.3(3) . . ? C16 Co1 P1 91.5(2) . . ? C18 Co1 P1 155.9(2) . . ? C19 Co1 P1 142.1(2) . . ? C15 Co1 I2 100.1(3) . . ? C17 Co1 I2 150.9(3) . . ? C16 Co1 I2 139.4(3) . . ? C18 Co1 I2 111.3(2) . . ? C19 Co1 I2 86.8(2) . . ? P1 Co1 I2 91.67(6) . . ? C15 Co1 I1 157.5(2) . . ? C17 Co1 I1 92.6(2) . . ? C16 Co1 I1 126.7(3) . . ? C18 Co1 I1 91.9(2) . . ? C19 Co1 I1 123.9(2) . . ? P1 Co1 I1 93.97(6) . . ? I2 Co1 I1 93.34(3) . . ? C36 Co2 C35 39.7(4) . . ? C36 Co2 C34 67.2(4) . . ? C35 Co2 C34 40.9(3) . . ? C36 Co2 C37 40.5(4) . . ? C35 Co2 C37 67.2(3) . . ? C34 Co2 C37 66.2(4) . . ? C36 Co2 C38 66.6(4) . . ? C35 Co2 C38 67.4(3) . . ? C34 Co2 C38 39.8(3) . . ? C37 Co2 C38 38.4(4) . . ? C36 Co2 P2 115.2(3) . . ? C35 Co2 P2 91.3(2) . . ? C34 Co2 P2 105.5(3) . . ? C37 Co2 P2 155.5(3) . . ? C38 Co2 P2 144.1(3) . . ? C36 Co2 I3 153.0(3) . . ? C35 Co2 I3 136.8(3) . . ? C34 Co2 I3 97.7(2) . . ? C37 Co2 I3 113.6(3) . . ? C38 Co2 I3 87.4(2) . . ? P2 Co2 I3 89.93(6) . . ? C36 Co2 I4 92.8(3) . . ? C35 Co2 I4 128.1(3) . . ? C34 Co2 I4 155.7(3) . . ? C37 Co2 I4 89.6(3) . . ? C38 Co2 I4 120.5(3) . . ? P2 Co2 I4 95.40(6) . . ? I3 Co2 I4 94.64(3) . . ? N1 P1 C9 104.6(3) . . ? N1 P1 C3 104.7(3) . . ? C9 P1 C3 106.2(3) . . ? N1 P1 Co1 109.8(2) . . ? C9 P1 Co1 116.9(2) . . ? C3 P1 Co1 113.7(2) . . ? N2 P2 C22 105.8(4) . . ? N2 P2 C28 103.5(3) . . ? C22 P2 C28 106.5(4) . . ? N2 P2 Co2 110.2(2) . . ? C22 P2 Co2 113.6(3) . . ? C28 P2 Co2 116.4(3) . . ? C1 N1 P1 128.4(5) . . ? C20 N2 P2 126.3(5) . . ? O1 C1 N1 124.0(6) . . ? O1 C1 C2 122.3(7) . . ? N1 C1 C2 113.7(6) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 120.4(6) . . ? C4 C3 P1 120.6(5) . . ? C8 C3 P1 118.9(5) . . ? C3 C4 C5 120.3(6) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.1(7) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 119.9 . . ? C7 C6 C5 120.0(7) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C6 C7 C8 120.5(7) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.8 . . ? C7 C8 C3 118.7(7) . . ? C7 C8 H8 120.6 . . ? C3 C8 H8 120.7 . . ? C14 C9 C10 119.3(7) . . ? C14 C9 P1 119.7(6) . . ? C10 C9 P1 121.0(5) . . ? C11 C10 C9 120.6(7) . . ? C11 C10 H10 119.7 . . ? C9 C10 H10 119.7 . . ? C10 C11 C12 120.0(8) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C13 118.6(9) . . ? C11 C12 H12 120.7 . . ? C13 C12 H12 120.7 . . ? C14 C13 C12 122.2(9) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C9 119.3(8) . . ? C13 C14 H14 120.4 . . ? C9 C14 H14 120.4 . . ? C16 C15 C19 107.5(7) . . ? C16 C15 Co1 70.1(4) . . ? C19 C15 Co1 71.7(4) . . ? C16 C15 H15 126.2 . . ? C19 C15 H15 126.3 . . ? Co1 C15 H15 123.6 . . ? C17 C16 C15 108.0(7) . . ? C17 C16 Co1 70.1(4) . . ? C15 C16 Co1 69.7(4) . . ? C17 C16 H16 126.0 . . ? C15 C16 H16 126.0 . . ? Co1 C16 H16 125.9 . . ? C16 C17 C18 108.1(7) . . ? C16 C17 Co1 70.3(4) . . ? C18 C17 Co1 71.5(4) . . ? C16 C17 H17 125.9 . . ? C18 C17 H17 125.9 . . ? Co1 C17 H17 124.0 . . ? C19 C18 C17 108.5(7) . . ? C19 C18 Co1 70.9(4) . . ? C17 C18 Co1 68.6(4) . . ? C19 C18 H18 125.8 . . ? C17 C18 H18 125.8 . . ? Co1 C18 H18 126.3 . . ? C18 C19 C15 107.8(7) . . ? C18 C19 Co1 70.5(4) . . ? C15 C19 Co1 68.1(4) . . ? C18 C19 H19 126.1 . . ? C15 C19 H19 126.1 . . ? Co1 C19 H19 126.9 . . ? O2 C20 N2 121.8(7) . . ? O2 C20 C21 124.2(7) . . ? N2 C20 C21 114.0(7) . . ? 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 . . ? C23 C22 C27 118.8(8) . . ? C23 C22 P2 121.9(6) . . ? C27 C22 P2 119.3(7) . . ? C22 C23 C24 121.0(9) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 121.0(10) . . ? C25 C24 H24 119.5 . . ? C23 C24 H24 119.5 . . ? C26 C25 C24 119.5(9) . . ? C26 C25 H25 120.3 . . ? C24 C25 H25 120.3 . . ? C25 C26 C27 122.7(10) . . ? C25 C26 H26 118.7 . . ? C27 C26 H26 118.7 . . ? C22 C27 C26 117.1(9) . . ? C22 C27 H27 121.5 . . ? C26 C27 H27 121.5 . . ? C33 C28 C29 119.6(7) . . ? C33 C28 P2 117.8(6) . . ? C29 C28 P2 122.4(6) . . ? C30 C29 C28 119.4(8) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C29 C30 C31 119.9(8) . . ? C29 C30 H30 120.0 . . ? C31 C30 H30 120.0 . . ? C32 C31 C30 120.5(7) . . ? C32 C31 H31 119.8 . . ? C30 C31 H31 119.8 . . ? C31 C32 C33 120.4(8) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? C28 C33 C32 120.0(8) . . ? C28 C33 H33 120.0 . . ? C32 C33 H33 120.0 . . ? C38 C34 C35 107.7(8) . . ? C38 C34 Co2 71.5(4) . . ? C35 C34 Co2 69.4(4) . . ? C38 C34 H34 126.1 . . ? C35 C34 H34 126.1 . . ? Co2 C34 H34 124.6 . . ? C36 C35 C34 107.0(7) . . ? C36 C35 Co2 70.1(4) . . ? C34 C35 Co2 69.7(4) . . ? C36 C35 H35 126.5 . . ? C34 C35 H35 126.5 . . ? Co2 C35 H35 125.4 . . ? C35 C36 C37 108.4(8) . . ? C35 C36 Co2 70.3(5) . . ? C37 C36 Co2 71.3(5) . . ? C35 C36 H36 125.8 . . ? C37 C36 H36 125.8 . . ? Co2 C36 H36 124.3 . . ? C38 C37 C36 108.1(8) . . ? C38 C37 Co2 70.9(5) . . ? C36 C37 Co2 68.2(5) . . ? C38 C37 H37 125.9 . . ? C36 C37 H37 125.9 . . ? Co2 C37 H37 126.5 . . ? C37 C38 C34 108.7(8) . . ? C37 C38 Co2 70.7(5) . . ? C34 C38 Co2 68.7(4) . . ? C37 C38 H38 125.7 . . ? C34 C38 H38 125.7 . . ? Co2 C38 H38 126.5 . . ? Cl4 C40 Cl4 108.2(7) . 2_667 ? Cl4 C40 H40A 110.4 . . ? Cl4 C40 H40A 110.3 2_667 . ? Cl4 C40 H40B 109.7 . . ? Cl4 C40 H40B 109.6 2_667 . ? H40A C40 H40B 108.6 . . ? C40 Cl4 C40 71.8(7) . 2_667 ? Cl2 C39 Cl3 112.4(7) . . ? Cl2 C39 H39A 109.1 . . ? Cl3 C39 H39A 109.1 . . ? Cl2 C39 H39B 109.1 . . ? Cl3 C39 H39B 109.1 . . ? H39A C39 H39B 107.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C15 Co1 P1 N1 151.0(3) . . . . ? C17 Co1 P1 N1 -138.1(3) . . . . ? C16 Co1 P1 N1 -170.3(3) . . . . ? C18 Co1 P1 N1 -146.9(6) . . . . ? C19 Co1 P1 N1 137.2(4) . . . . ? I2 Co1 P1 N1 50.2(2) . . . . ? I1 Co1 P1 N1 -43.3(2) . . . . ? C15 Co1 P1 C9 -90.2(4) . . . . ? C17 Co1 P1 C9 -19.3(4) . . . . ? C16 Co1 P1 C9 -51.4(4) . . . . ? C18 Co1 P1 C9 -28.1(6) . . . . ? C19 Co1 P1 C9 -104.0(4) . . . . ? I2 Co1 P1 C9 169.0(3) . . . . ? I1 Co1 P1 C9 75.5(3) . . . . ? C15 Co1 P1 C3 34.1(4) . . . . ? C17 Co1 P1 C3 105.0(4) . . . . ? C16 Co1 P1 C3 72.9(4) . . . . ? C18 Co1 P1 C3 96.3(6) . . . . ? C19 Co1 P1 C3 20.3(4) . . . . ? I2 Co1 P1 C3 -66.7(2) . . . . ? I1 Co1 P1 C3 -160.1(2) . . . . ? C36 Co2 P2 N2 -134.2(4) . . . . ? C35 Co2 P2 N2 -167.0(3) . . . . ? C34 Co2 P2 N2 154.1(3) . . . . ? C37 Co2 P2 N2 -139.6(7) . . . . ? C38 Co2 P2 N2 141.6(5) . . . . ? I3 Co2 P2 N2 56.2(2) . . . . ? I4 Co2 P2 N2 -38.5(2) . . . . ? C36 Co2 P2 C22 107.3(4) . . . . ? C35 Co2 P2 C22 74.5(4) . . . . ? C34 Co2 P2 C22 35.6(4) . . . . ? C37 Co2 P2 C22 101.9(7) . . . . ? C38 Co2 P2 C22 23.1(5) . . . . ? I3 Co2 P2 C22 -62.4(3) . . . . ? I4 Co2 P2 C22 -157.0(3) . . . . ? C36 Co2 P2 C28 -16.9(4) . . . . ? C35 Co2 P2 C28 -49.7(4) . . . . ? C34 Co2 P2 C28 -88.6(4) . . . . ? C37 Co2 P2 C28 -22.3(7) . . . . ? C38 Co2 P2 C28 -101.1(5) . . . . ? I3 Co2 P2 C28 173.5(3) . . . . ? I4 Co2 P2 C28 78.8(3) . . . . ? C9 P1 N1 C1 60.9(7) . . . . ? C3 P1 N1 C1 -50.6(7) . . . . ? Co1 P1 N1 C1 -173.0(6) . . . . ? C22 P2 N2 C20 -60.8(7) . . . . ? C28 P2 N2 C20 50.9(7) . . . . ? Co2 P2 N2 C20 176.0(5) . . . . ? P1 N1 C1 O1 3.1(11) . . . . ? P1 N1 C1 C2 -177.6(6) . . . . ? N1 P1 C3 C4 -27.7(7) . . . . ? C9 P1 C3 C4 -138.0(6) . . . . ? Co1 P1 C3 C4 92.1(6) . . . . ? N1 P1 C3 C8 156.5(6) . . . . ? C9 P1 C3 C8 46.1(7) . . . . ? Co1 P1 C3 C8 -83.7(6) . . . . ? C8 C3 C4 C5 -1.3(12) . . . . ? P1 C3 C4 C5 -177.0(6) . . . . ? C3 C4 C5 C6 -0.4(12) . . . . ? C4 C5 C6 C7 2.0(13) . . . . ? C5 C6 C7 C8 -1.9(14) . . . . ? C6 C7 C8 C3 0.3(13) . . . . ? C4 C3 C8 C7 1.3(12) . . . . ? P1 C3 C8 C7 177.1(6) . . . . ? N1 P1 C9 C14 99.4(7) . . . . ? C3 P1 C9 C14 -150.2(7) . . . . ? Co1 P1 C9 C14 -22.2(8) . . . . ? N1 P1 C9 C10 -78.5(7) . . . . ? C3 P1 C9 C10 31.8(7) . . . . ? Co1 P1 C9 C10 159.9(5) . . . . ? C14 C9 C10 C11 -0.7(12) . . . . ? P1 C9 C10 C11 177.3(7) . . . . ? C9 C10 C11 C12 1.2(14) . . . . ? C10 C11 C12 C13 -1.9(16) . . . . ? C11 C12 C13 C14 2.2(17) . . . . ? C12 C13 C14 C9 -1.7(17) . . . . ? C10 C9 C14 C13 0.8(14) . . . . ? P1 C9 C14 C13 -177.2(8) . . . . ? C17 Co1 C15 C16 -37.3(5) . . . . ? C18 Co1 C15 C16 -80.9(5) . . . . ? C19 Co1 C15 C16 -117.1(6) . . . . ? P1 Co1 C15 C16 75.9(4) . . . . ? I2 Co1 C15 C16 170.1(4) . . . . ? I1 Co1 C15 C16 -64.1(9) . . . . ? C17 Co1 C15 C19 79.9(5) . . . . ? C16 Co1 C15 C19 117.1(6) . . . . ? C18 Co1 C15 C19 36.3(5) . . . . ? P1 Co1 C15 C19 -166.9(4) . . . . ? I2 Co1 C15 C19 -72.7(4) . . . . ? I1 Co1 C15 C19 53.1(10) . . . . ? C19 C15 C16 C17 -2.5(8) . . . . ? Co1 C15 C16 C17 59.8(5) . . . . ? C19 C15 C16 Co1 -62.3(5) . . . . ? C15 Co1 C16 C17 -119.0(7) . . . . ? C18 Co1 C16 C17 -38.2(5) . . . . ? C19 Co1 C16 C17 -80.3(5) . . . . ? P1 Co1 C16 C17 131.6(5) . . . . ? I2 Co1 C16 C17 -134.1(5) . . . . ? I1 Co1 C16 C17 35.6(6) . . . . ? C17 Co1 C16 C15 119.0(7) . . . . ? C18 Co1 C16 C15 80.9(5) . . . . ? C19 Co1 C16 C15 38.7(5) . . . . ? P1 Co1 C16 C15 -109.3(4) . . . . ? I2 Co1 C16 C15 -15.1(6) . . . . ? I1 Co1 C16 C15 154.6(4) . . . . ? C15 C16 C17 C18 2.2(9) . . . . ? Co1 C16 C17 C18 61.8(5) . . . . ? C15 C16 C17 Co1 -59.6(5) . . . . ? C15 Co1 C17 C16 37.8(5) . . . . ? C18 Co1 C17 C16 118.0(7) . . . . ? C19 Co1 C17 C16 81.7(5) . . . . ? P1 Co1 C17 C16 -56.5(5) . . . . ? I2 Co1 C17 C16 106.3(6) . . . . ? I1 Co1 C17 C16 -152.2(5) . . . . ? C15 Co1 C17 C18 -80.2(5) . . . . ? C16 Co1 C17 C18 -118.0(7) . . . . ? C19 Co1 C17 C18 -36.3(5) . . . . ? P1 Co1 C17 C18 -174.4(4) . . . . ? I2 Co1 C17 C18 -11.7(8) . . . . ? I1 Co1 C17 C18 89.9(4) . . . . ? C16 C17 C18 C19 -1.1(9) . . . . ? Co1 C17 C18 C19 60.0(5) . . . . ? C16 C17 C18 Co1 -61.0(5) . . . . ? C15 Co1 C18 C19 -37.8(5) . . . . ? C17 Co1 C18 C19 -119.7(7) . . . . ? C16 Co1 C18 C19 -81.8(5) . . . . ? P1 Co1 C18 C19 -107.4(6) . . . . ? I2 Co1 C18 C19 54.2(5) . . . . ? I1 Co1 C18 C19 148.6(4) . . . . ? C15 Co1 C18 C17 81.9(5) . . . . ? C16 Co1 C18 C17 37.9(5) . . . . ? C19 Co1 C18 C17 119.7(7) . . . . ? P1 Co1 C18 C17 12.3(9) . . . . ? I2 Co1 C18 C17 173.9(4) . . . . ? I1 Co1 C18 C17 -91.8(4) . . . . ? C17 C18 C19 C15 -0.5(8) . . . . ? Co1 C18 C19 C15 58.0(5) . . . . ? C17 C18 C19 Co1 -58.5(5) . . . . ? C16 C15 C19 C18 1.9(8) . . . . ? Co1 C15 C19 C18 -59.5(5) . . . . ? C16 C15 C19 Co1 61.3(5) . . . . ? C15 Co1 C19 C18 119.5(7) . . . . ? C17 Co1 C19 C18 37.5(5) . . . . ? C16 Co1 C19 C18 80.9(5) . . . . ? P1 Co1 C19 C18 140.5(4) . . . . ? I2 Co1 C19 C18 -130.8(4) . . . . ? I1 Co1 C19 C18 -38.9(5) . . . . ? C17 Co1 C19 C15 -82.0(5) . . . . ? C16 Co1 C19 C15 -38.7(5) . . . . ? C18 Co1 C19 C15 -119.5(7) . . . . ? P1 Co1 C19 C15 21.0(6) . . . . ? I2 Co1 C19 C15 109.7(5) . . . . ? I1 Co1 C19 C15 -158.4(4) . . . . ? P2 N2 C20 O2 9.6(11) . . . . ? P2 N2 C20 C21 -171.2(6) . . . . ? N2 P2 C22 C23 -16.2(8) . . . . ? C28 P2 C22 C23 -125.9(7) . . . . ? Co2 P2 C22 C23 104.8(7) . . . . ? N2 P2 C22 C27 167.1(7) . . . . ? C28 P2 C22 C27 57.5(8) . . . . ? Co2 P2 C22 C27 -71.9(7) . . . . ? C27 C22 C23 C24 0.7(13) . . . . ? P2 C22 C23 C24 -176.0(7) . . . . ? C22 C23 C24 C25 1.7(15) . . . . ? C23 C24 C25 C26 -3.3(16) . . . . ? C24 C25 C26 C27 2.4(17) . . . . ? C23 C22 C27 C26 -1.5(13) . . . . ? P2 C22 C27 C26 175.3(7) . . . . ? C25 C26 C27 C22 -0.1(16) . . . . ? N2 P2 C28 C33 79.3(6) . . . . ? C22 P2 C28 C33 -169.5(6) . . . . ? Co2 P2 C28 C33 -41.7(6) . . . . ? N2 P2 C28 C29 -96.2(7) . . . . ? C22 P2 C28 C29 15.1(8) . . . . ? Co2 P2 C28 C29 142.9(6) . . . . ? C33 C28 C29 C30 0.5(13) . . . . ? P2 C28 C29 C30 175.8(7) . . . . ? C28 C29 C30 C31 -4.1(14) . . . . ? C29 C30 C31 C32 5.2(15) . . . . ? C30 C31 C32 C33 -2.6(13) . . . . ? C29 C28 C33 C32 2.1(11) . . . . ? P2 C28 C33 C32 -173.4(6) . . . . ? C31 C32 C33 C28 -1.1(12) . . . . ? C36 Co2 C34 C38 80.2(6) . . . . ? C35 Co2 C34 C38 118.0(8) . . . . ? C37 Co2 C34 C38 35.9(5) . . . . ? P2 Co2 C34 C38 -168.5(5) . . . . ? I3 Co2 C34 C38 -76.5(5) . . . . ? I4 Co2 C34 C38 43.3(9) . . . . ? C36 Co2 C34 C35 -37.8(5) . . . . ? C37 Co2 C34 C35 -82.0(6) . . . . ? C38 Co2 C34 C35 -118.0(8) . . . . ? P2 Co2 C34 C35 73.5(5) . . . . ? I3 Co2 C34 C35 165.6(5) . . . . ? I4 Co2 C34 C35 -74.6(8) . . . . ? C38 C34 C35 C36 -1.1(9) . . . . ? Co2 C34 C35 C36 60.4(5) . . . . ? C38 C34 C35 Co2 -61.6(5) . . . . ? C34 Co2 C35 C36 -117.8(7) . . . . ? C37 Co2 C35 C36 -38.3(5) . . . . ? C38 Co2 C35 C36 -80.0(6) . . . . ? P2 Co2 C35 C36 129.8(5) . . . . ? I3 Co2 C35 C36 -139.0(5) . . . . ? I4 Co2 C35 C36 31.9(6) . . . . ? C36 Co2 C35 C34 117.8(7) . . . . ? C37 Co2 C35 C34 79.5(6) . . . . ? C38 Co2 C35 C34 37.8(5) . . . . ? P2 Co2 C35 C34 -112.4(5) . . . . ? I3 Co2 C35 C34 -21.2(6) . . . . ? I4 Co2 C35 C34 149.7(4) . . . . ? C34 C35 C36 C37 1.2(9) . . . . ? Co2 C35 C36 C37 61.4(5) . . . . ? C34 C35 C36 Co2 -60.2(5) . . . . ? C34 Co2 C36 C35 38.9(5) . . . . ? C37 Co2 C36 C35 118.5(7) . . . . ? C38 Co2 C36 C35 82.4(5) . . . . ? P2 Co2 C36 C35 -58.1(5) . . . . ? I3 Co2 C36 C35 98.6(7) . . . . ? I4 Co2 C36 C35 -155.4(5) . . . . ? C35 Co2 C36 C37 -118.5(7) . . . . ? C34 Co2 C36 C37 -79.5(6) . . . . ? C38 Co2 C36 C37 -36.1(5) . . . . ? P2 Co2 C36 C37 -176.6(4) . . . . ? I3 Co2 C36 C37 -19.8(9) . . . . ? I4 Co2 C36 C37 86.1(5) . . . . ? C35 C36 C37 C38 -0.8(9) . . . . ? Co2 C36 C37 C38 59.9(6) . . . . ? C35 C36 C37 Co2 -60.7(5) . . . . ? C36 Co2 C37 C38 -119.5(7) . . . . ? C35 Co2 C37 C38 -82.0(5) . . . . ? C34 Co2 C37 C38 -37.3(5) . . . . ? P2 Co2 C37 C38 -112.0(7) . . . . ? I3 Co2 C37 C38 50.8(5) . . . . ? I4 Co2 C37 C38 145.7(5) . . . . ? C35 Co2 C37 C36 37.5(5) . . . . ? C34 Co2 C37 C36 82.2(6) . . . . ? C38 Co2 C37 C36 119.5(7) . . . . ? P2 Co2 C37 C36 7.5(10) . . . . ? I3 Co2 C37 C36 170.3(4) . . . . ? I4 Co2 C37 C36 -94.8(5) . . . . ? C36 C37 C38 C34 0.1(9) . . . . ? Co2 C37 C38 C34 58.3(5) . . . . ? C36 C37 C38 Co2 -58.3(5) . . . . ? C35 C34 C38 C37 0.6(9) . . . . ? Co2 C34 C38 C37 -59.6(6) . . . . ? C35 C34 C38 Co2 60.2(5) . . . . ? C36 Co2 C38 C37 38.0(5) . . . . ? C35 Co2 C38 C37 81.3(6) . . . . ? C34 Co2 C38 C37 120.0(7) . . . . ? P2 Co2 C38 C37 139.1(5) . . . . ? I3 Co2 C38 C37 -134.7(5) . . . . ? I4 Co2 C38 C37 -40.8(6) . . . . ? C36 Co2 C38 C34 -82.0(6) . . . . ? C35 Co2 C38 C34 -38.8(5) . . . . ? C37 Co2 C38 C34 -120.0(7) . . . . ? P2 Co2 C38 C34 19.1(7) . . . . ? I3 Co2 C38 C34 105.3(5) . . . . ? I4 Co2 C38 C34 -160.9(4) . . . . ? Cl4 C40 Cl4 C40 0.000(2) 2_667 . . 2_667 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.07 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.977 _refine_diff_density_min -1.592 _refine_diff_density_rms 0.206 # Attachment 'Complex4.cif' data_Complex4 _database_code_depnum_ccdc_archive 'CCDC 698956' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H18 Co I N O P' _chemical_formula_sum 'C19 H18 Co I N O P' _chemical_formula_weight 493.14 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 12.6820(2) _cell_length_b 8.3580(2) _cell_length_c 17.9100(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.1030(13) _cell_angle_gamma 90.00 _cell_volume 1868.95(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5404 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour black _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.753 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 968 _exptl_absorpt_coefficient_mu 2.661 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9352 _diffrn_reflns_av_R_equivalents 0.0298 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 30.00 _reflns_number_total 5456 _reflns_number_gt 4025 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0387P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5456 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0886 _refine_ls_wR_factor_gt 0.0793 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.003 _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 I1 I 0.418629(15) 1.12647(2) 0.141732(10) 0.03266(8) Uani 1 1 d . . . Co1 Co 0.39002(3) 0.83740(5) 0.093217(19) 0.02287(10) Uani 1 1 d . . . P1 P 0.23854(5) 0.80641(9) 0.13434(4) 0.02259(15) Uani 1 1 d . . . O1 O 0.29664(14) 0.9126(2) 0.00373(9) 0.0272(4) Uani 1 1 d . . . N1 N 0.15032(18) 0.8919(3) 0.06517(12) 0.0269(5) Uani 1 1 d . . . C1 C 0.1963(2) 0.9304(3) 0.00720(14) 0.0261(6) Uani 1 1 d . . . C2 C 0.1286(2) 0.9994(4) -0.06313(14) 0.0392(8) Uani 1 1 d . . . H2A H 0.1581 1.1029 -0.0749 0.059 Uiso 1 1 calc . . . H2B H 0.0550 1.0141 -0.0544 0.059 Uiso 1 1 calc . . . H2C H 0.1286 0.9260 -0.1058 0.059 Uiso 1 1 calc . . . C3 C 0.2155(2) 0.8858(3) 0.22437(14) 0.0235(6) Uani 1 1 d . . . C4 C 0.2991(2) 0.9062(4) 0.28452(15) 0.0309(7) Uani 1 1 d . . . H4 H 0.3703 0.8809 0.2787 0.037 Uiso 1 1 calc . . . C5 C 0.2789(2) 0.9635(4) 0.35330(14) 0.0389(8) Uani 1 1 d . . . H5 H 0.3365 0.9754 0.3947 0.047 Uiso 1 1 calc . . . C6 C 0.1770(3) 1.0032(4) 0.36248(14) 0.0405(8) Uani 1 1 d . . . H6 H 0.1645 1.0444 0.4096 0.049 Uiso 1 1 calc . . . C7 C 0.0924(2) 0.9829(4) 0.30259(17) 0.0397(8) Uani 1 1 d . . . H7 H 0.0217 1.0104 0.3086 0.048 Uiso 1 1 calc . . . C8 C 0.1112(2) 0.9224(4) 0.23398(15) 0.0314(6) Uani 1 1 d . . . H8 H 0.0530 0.9058 0.1935 0.038 Uiso 1 1 calc . . . C9 C 0.1929(2) 0.6005(3) 0.13822(15) 0.0261(6) Uani 1 1 d . . . C10 C 0.1385(2) 0.5305(4) 0.07238(15) 0.0338(7) Uani 1 1 d . . . H10 H 0.1225 0.5921 0.0272 0.041 Uiso 1 1 calc . . . C11 C 0.1072(3) 0.3714(4) 0.07192(19) 0.0397(8) Uani 1 1 d . . . H11 H 0.0701 0.3242 0.0266 0.048 Uiso 1 1 calc . . . C12 C 0.1301(2) 0.2819(4) 0.1374(2) 0.0409(8) Uani 1 1 d . . . H12 H 0.1089 0.1729 0.1373 0.049 Uiso 1 1 calc . . . C13 C 0.1843(3) 0.3515(4) 0.20378(18) 0.0385(8) Uani 1 1 d . . . H13 H 0.2000 0.2899 0.2489 0.046 Uiso 1 1 calc . . . C14 C 0.2152(2) 0.5096(4) 0.20410(14) 0.0314(6) Uani 1 1 d . . . H14 H 0.2519 0.5568 0.2496 0.038 Uiso 1 1 calc . . . C15 C 0.5374(2) 0.7666(4) 0.15088(16) 0.0345(7) Uani 1 1 d . . . H15 H 0.5746 0.8165 0.1955 0.041 Uiso 1 1 calc . . . C16 C 0.4781(2) 0.7058(4) 0.02610(16) 0.0330(7) Uani 1 1 d . . . H16 H 0.4689 0.7052 -0.0277 0.040 Uiso 1 1 calc . . . C17 C 0.5475(2) 0.8061(4) 0.07424(17) 0.0337(7) Uani 1 1 d . . . H17 H 0.5930 0.8857 0.0592 0.040 Uiso 1 1 calc . . . C18 C 0.4233(2) 0.6044(3) 0.07090(16) 0.0309(7) Uani 1 1 d . . . H18 H 0.3703 0.5269 0.0523 0.037 Uiso 1 1 calc . . . C19 C 0.4623(2) 0.6407(3) 0.14832(15) 0.0300(7) Uani 1 1 d . . . H19 H 0.4417 0.5894 0.1908 0.036 Uiso 1 1 calc . . . 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 I1 0.03875(13) 0.03108(13) 0.03009(12) -0.00326(8) 0.01141(9) -0.00717(8) Co1 0.02091(19) 0.0272(2) 0.02119(18) 0.00206(15) 0.00544(14) 0.00174(15) P1 0.0218(3) 0.0242(4) 0.0223(3) 0.0015(3) 0.0054(3) 0.0006(3) O1 0.0259(10) 0.0344(12) 0.0217(9) 0.0042(8) 0.0056(8) 0.0017(9) N1 0.0262(12) 0.0300(14) 0.0244(11) 0.0016(10) 0.0039(9) 0.0014(10) C1 0.0272(14) 0.0235(15) 0.0260(13) -0.0008(11) 0.0000(11) -0.0010(12) C2 0.0346(16) 0.054(2) 0.0273(14) 0.0086(15) 0.0009(12) 0.0057(15) C3 0.0259(14) 0.0240(15) 0.0219(12) 0.0011(10) 0.0073(11) -0.0018(11) C4 0.0279(15) 0.0381(19) 0.0265(14) 0.0003(12) 0.0041(11) -0.0008(13) C5 0.0456(18) 0.046(2) 0.0240(14) -0.0005(14) 0.0025(13) -0.0098(16) C6 0.053(2) 0.047(2) 0.0261(14) -0.0018(15) 0.0199(14) -0.0065(17) C7 0.0392(17) 0.042(2) 0.0438(16) -0.0008(16) 0.0241(14) -0.0020(15) C8 0.0269(14) 0.0385(18) 0.0294(14) 0.0001(13) 0.0068(12) -0.0008(13) C9 0.0221(13) 0.0261(16) 0.0318(14) 0.0004(11) 0.0091(11) 0.0024(11) C10 0.0381(16) 0.0324(18) 0.0319(14) -0.0040(13) 0.0090(12) -0.0048(14) C11 0.0434(19) 0.035(2) 0.0414(18) -0.0115(14) 0.0094(15) -0.0054(14) C12 0.0381(17) 0.0223(17) 0.064(2) 0.0004(15) 0.0143(16) -0.0010(14) C13 0.0362(17) 0.0324(19) 0.0479(19) 0.0114(14) 0.0098(15) 0.0000(14) C14 0.0266(14) 0.0320(18) 0.0342(14) 0.0064(13) 0.0018(12) 0.0002(12) C15 0.0233(14) 0.045(2) 0.0347(15) 0.0059(14) 0.0020(12) 0.0074(13) C16 0.0343(16) 0.0355(18) 0.0329(15) 0.0002(13) 0.0155(13) 0.0119(14) C17 0.0237(14) 0.0365(19) 0.0441(17) 0.0067(14) 0.0151(13) 0.0053(13) C18 0.0291(15) 0.0264(17) 0.0388(16) -0.0011(12) 0.0101(13) 0.0041(12) C19 0.0313(15) 0.0291(17) 0.0319(15) 0.0113(12) 0.0115(12) 0.0085(12) _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 I1 Co1 2.5716(4) . ? Co1 O1 1.9238(18) . ? Co1 C18 2.047(3) . ? Co1 C19 2.050(3) . ? Co1 C15 2.057(3) . ? Co1 C16 2.091(3) . ? Co1 C17 2.101(3) . ? Co1 P1 2.1901(7) . ? P1 N1 1.676(2) . ? P1 C3 1.814(3) . ? P1 C9 1.821(3) . ? O1 C1 1.294(3) . ? N1 C1 1.317(3) . ? C1 C2 1.509(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.383(4) . ? C3 C8 1.398(4) . ? C4 C5 1.387(4) . ? C4 H4 0.9500 . ? C5 C6 1.371(4) . ? C5 H5 0.9500 . ? C6 C7 1.388(4) . ? C6 H6 0.9500 . ? C7 C8 1.387(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.387(4) . ? C9 C14 1.390(4) . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 C12 1.379(5) . ? C11 H11 0.9500 . ? C12 C13 1.391(5) . ? C12 H12 0.9500 . ? C13 C14 1.379(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C19 1.414(4) . ? C15 C17 1.439(4) . ? C15 H15 0.9500 . ? C16 C17 1.399(4) . ? C16 C18 1.429(4) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 C19 1.421(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? 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 O1 Co1 C18 105.43(10) . . ? O1 Co1 C19 145.23(11) . . ? C18 Co1 C19 40.59(12) . . ? O1 Co1 C15 152.20(10) . . ? C18 Co1 C15 67.93(13) . . ? C19 Co1 C15 40.29(12) . . ? O1 Co1 C16 90.33(10) . . ? C18 Co1 C16 40.38(11) . . ? C19 Co1 C16 67.41(11) . . ? C15 Co1 C16 66.89(12) . . ? O1 Co1 C17 111.70(10) . . ? C18 Co1 C17 67.40(12) . . ? C19 Co1 C17 67.68(12) . . ? C15 Co1 C17 40.50(11) . . ? C16 Co1 C17 38.98(12) . . ? O1 Co1 P1 82.57(5) . . ? C18 Co1 P1 100.14(8) . . ? C19 Co1 P1 95.05(8) . . ? C15 Co1 P1 124.77(8) . . ? C16 Co1 P1 136.02(9) . . ? C17 Co1 P1 162.72(9) . . ? O1 Co1 I1 90.24(6) . . ? C18 Co1 I1 159.75(8) . . ? C19 Co1 I1 124.49(9) . . ? C15 Co1 I1 92.22(10) . . ? C16 Co1 I1 129.08(9) . . ? C17 Co1 I1 95.14(9) . . ? P1 Co1 I1 94.45(2) . . ? N1 P1 C3 108.08(12) . . ? N1 P1 C9 104.81(12) . . ? C3 P1 C9 102.11(12) . . ? N1 P1 Co1 102.25(8) . . ? C3 P1 Co1 122.91(9) . . ? C9 P1 Co1 115.34(9) . . ? C1 O1 Co1 117.68(15) . . ? C1 N1 P1 110.89(19) . . ? O1 C1 N1 125.8(2) . . ? O1 C1 C2 115.1(2) . . ? N1 C1 C2 119.1(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 119.3(2) . . ? C4 C3 P1 121.1(2) . . ? C8 C3 P1 119.5(2) . . ? C3 C4 C5 119.9(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? C6 C5 C4 121.0(3) . . ? C6 C5 H5 119.5 . . ? C4 C5 H5 119.5 . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.0(3) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C3 120.1(3) . . ? C7 C8 H8 119.9 . . ? C3 C8 H8 119.9 . . ? C10 C9 C14 119.2(3) . . ? C10 C9 P1 118.7(2) . . ? C14 C9 P1 122.0(2) . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 119.8(3) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.1(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C9 120.3(3) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C19 C15 C17 108.2(3) . . ? C19 C15 Co1 69.57(16) . . ? C17 C15 Co1 71.38(16) . . ? C19 C15 H15 125.9 . . ? C17 C15 H15 125.9 . . ? Co1 C15 H15 124.7 . . ? C17 C16 C18 109.0(3) . . ? C17 C16 Co1 70.87(16) . . ? C18 C16 Co1 68.13(15) . . ? C17 C16 H16 125.5 . . ? C18 C16 H16 125.5 . . ? Co1 C16 H16 127.1 . . ? C16 C17 C15 107.3(3) . . ? C16 C17 Co1 70.15(15) . . ? C15 C17 Co1 68.12(14) . . ? C16 C17 H17 126.3 . . ? C15 C17 H17 126.3 . . ? Co1 C17 H17 126.9 . . ? C19 C18 C16 107.5(3) . . ? C19 C18 Co1 69.81(16) . . ? C16 C18 Co1 71.49(17) . . ? C19 C18 H18 126.3 . . ? C16 C18 H18 126.3 . . ? Co1 C18 H18 124.1 . . ? C15 C19 C18 107.9(2) . . ? C15 C19 Co1 70.14(16) . . ? C18 C19 Co1 69.60(16) . . ? C15 C19 H19 126.0 . . ? C18 C19 H19 126.0 . . ? Co1 C19 H19 125.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Co1 P1 N1 -7.38(10) . . . . ? C18 Co1 P1 N1 -111.82(12) . . . . ? C19 Co1 P1 N1 -152.48(12) . . . . ? C15 Co1 P1 N1 178.09(14) . . . . ? C16 Co1 P1 N1 -90.11(15) . . . . ? C17 Co1 P1 N1 -154.2(3) . . . . ? I1 Co1 P1 N1 82.28(9) . . . . ? O1 Co1 P1 C3 -128.62(12) . . . . ? C18 Co1 P1 C3 126.94(14) . . . . ? C19 Co1 P1 C3 86.28(14) . . . . ? C15 Co1 P1 C3 56.85(16) . . . . ? C16 Co1 P1 C3 148.65(15) . . . . ? C17 Co1 P1 C3 84.6(3) . . . . ? I1 Co1 P1 C3 -38.97(11) . . . . ? O1 Co1 P1 C9 105.71(12) . . . . ? C18 Co1 P1 C9 1.28(13) . . . . ? C19 Co1 P1 C9 -39.38(13) . . . . ? C15 Co1 P1 C9 -68.82(16) . . . . ? C16 Co1 P1 C9 22.99(16) . . . . ? C17 Co1 P1 C9 -41.1(3) . . . . ? I1 Co1 P1 C9 -164.63(10) . . . . ? C18 Co1 O1 C1 105.9(2) . . . . ? C19 Co1 O1 C1 95.5(2) . . . . ? C15 Co1 O1 C1 177.7(3) . . . . ? C16 Co1 O1 C1 143.8(2) . . . . ? C17 Co1 O1 C1 177.3(2) . . . . ? P1 Co1 O1 C1 7.34(19) . . . . ? I1 Co1 O1 C1 -87.11(19) . . . . ? C3 P1 N1 C1 138.3(2) . . . . ? C9 P1 N1 C1 -113.3(2) . . . . ? Co1 P1 N1 C1 7.4(2) . . . . ? Co1 O1 C1 N1 -4.7(4) . . . . ? Co1 O1 C1 C2 176.4(2) . . . . ? P1 N1 C1 O1 -2.8(4) . . . . ? P1 N1 C1 C2 176.1(2) . . . . ? N1 P1 C3 C4 -147.1(2) . . . . ? C9 P1 C3 C4 102.7(3) . . . . ? Co1 P1 C3 C4 -28.6(3) . . . . ? N1 P1 C3 C8 34.8(3) . . . . ? C9 P1 C3 C8 -75.3(3) . . . . ? Co1 P1 C3 C8 153.3(2) . . . . ? C8 C3 C4 C5 -0.4(5) . . . . ? P1 C3 C4 C5 -178.5(2) . . . . ? C3 C4 C5 C6 -1.1(5) . . . . ? C4 C5 C6 C7 1.3(5) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C3 -1.7(5) . . . . ? C4 C3 C8 C7 1.8(5) . . . . ? P1 C3 C8 C7 179.9(2) . . . . ? N1 P1 C9 C10 29.3(2) . . . . ? C3 P1 C9 C10 142.0(2) . . . . ? Co1 P1 C9 C10 -82.3(2) . . . . ? N1 P1 C9 C14 -153.7(2) . . . . ? C3 P1 C9 C14 -41.0(3) . . . . ? Co1 P1 C9 C14 94.7(2) . . . . ? C14 C9 C10 C11 -0.4(4) . . . . ? P1 C9 C10 C11 176.7(2) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C11 C12 C13 0.1(5) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C12 C13 C14 C9 -0.2(5) . . . . ? C10 C9 C14 C13 0.5(4) . . . . ? P1 C9 C14 C13 -176.5(2) . . . . ? O1 Co1 C15 C19 -119.1(2) . . . . ? C18 Co1 C15 C19 -37.91(17) . . . . ? C16 Co1 C15 C19 -81.80(19) . . . . ? C17 Co1 C15 C19 -118.5(3) . . . . ? P1 Co1 C15 C19 49.2(2) . . . . ? I1 Co1 C15 C19 146.18(16) . . . . ? O1 Co1 C15 C17 -0.6(4) . . . . ? C18 Co1 C15 C17 80.6(2) . . . . ? C19 Co1 C15 C17 118.5(3) . . . . ? C16 Co1 C15 C17 36.69(18) . . . . ? P1 Co1 C15 C17 167.70(15) . . . . ? I1 Co1 C15 C17 -95.33(18) . . . . ? O1 Co1 C16 C17 125.50(18) . . . . ? C18 Co1 C16 C17 -120.7(3) . . . . ? C19 Co1 C16 C17 -81.97(19) . . . . ? C15 Co1 C16 C17 -38.08(18) . . . . ? P1 Co1 C16 C17 -154.88(14) . . . . ? I1 Co1 C16 C17 34.9(2) . . . . ? O1 Co1 C16 C18 -113.82(17) . . . . ? C19 Co1 C16 C18 38.71(18) . . . . ? C15 Co1 C16 C18 82.60(19) . . . . ? C17 Co1 C16 C18 120.7(3) . . . . ? P1 Co1 C16 C18 -34.2(2) . . . . ? I1 Co1 C16 C18 155.60(14) . . . . ? C18 C16 C17 C15 0.6(3) . . . . ? Co1 C16 C17 C15 58.14(19) . . . . ? C18 C16 C17 Co1 -57.6(2) . . . . ? C19 C15 C17 C16 0.7(3) . . . . ? Co1 C15 C17 C16 -59.4(2) . . . . ? C19 C15 C17 Co1 60.11(19) . . . . ? O1 Co1 C17 C16 -61.19(19) . . . . ? C18 Co1 C17 C16 37.12(18) . . . . ? C19 Co1 C17 C16 81.21(19) . . . . ? C15 Co1 C17 C16 119.1(3) . . . . ? P1 Co1 C17 C16 83.0(3) . . . . ? I1 Co1 C17 C16 -153.50(16) . . . . ? O1 Co1 C17 C15 179.70(18) . . . . ? C18 Co1 C17 C15 -82.0(2) . . . . ? C19 Co1 C17 C15 -37.90(19) . . . . ? C16 Co1 C17 C15 -119.1(3) . . . . ? P1 Co1 C17 C15 -36.1(4) . . . . ? I1 Co1 C17 C15 87.39(19) . . . . ? C17 C16 C18 C19 -1.6(3) . . . . ? Co1 C16 C18 C19 -60.85(19) . . . . ? C17 C16 C18 Co1 59.2(2) . . . . ? O1 Co1 C18 C19 -170.93(16) . . . . ? C15 Co1 C18 C19 37.64(17) . . . . ? C16 Co1 C18 C19 117.4(2) . . . . ? C17 Co1 C18 C19 81.57(18) . . . . ? P1 Co1 C18 C19 -85.91(16) . . . . ? I1 Co1 C18 C19 49.5(3) . . . . ? O1 Co1 C18 C16 71.62(18) . . . . ? C19 Co1 C18 C16 -117.4(2) . . . . ? C15 Co1 C18 C16 -79.81(18) . . . . ? C17 Co1 C18 C16 -35.87(17) . . . . ? P1 Co1 C18 C16 156.64(16) . . . . ? I1 Co1 C18 C16 -67.9(3) . . . . ? C17 C15 C19 C18 -1.7(3) . . . . ? Co1 C15 C19 C18 59.6(2) . . . . ? C17 C15 C19 Co1 -61.2(2) . . . . ? C16 C18 C19 C15 2.0(3) . . . . ? Co1 C18 C19 C15 -59.9(2) . . . . ? C16 C18 C19 Co1 61.9(2) . . . . ? O1 Co1 C19 C15 134.38(19) . . . . ? C18 Co1 C19 C15 118.9(2) . . . . ? C16 Co1 C19 C15 80.42(19) . . . . ? C17 Co1 C19 C15 38.09(18) . . . . ? P1 Co1 C19 C15 -141.37(16) . . . . ? I1 Co1 C19 C15 -42.44(19) . . . . ? O1 Co1 C19 C18 15.5(3) . . . . ? C15 Co1 C19 C18 -118.9(2) . . . . ? C16 Co1 C19 C18 -38.52(17) . . . . ? C17 Co1 C19 C18 -80.84(18) . . . . ? P1 Co1 C19 C18 99.70(16) . . . . ? I1 Co1 C19 C18 -161.37(13) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.892 _refine_diff_density_min -1.093 _refine_diff_density_rms 0.119 # Attachment 'Complex5.cif' data_Complex5 _database_code_depnum_ccdc_archive 'CCDC 698957' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H40 Ni O2 P2' _chemical_formula_sum 'C28 H40 Ni O2 P2' _chemical_formula_weight 529.25 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3590(2) _cell_length_b 10.0440(4) _cell_length_c 10.1440(3) _cell_angle_alpha 63.3780(16) _cell_angle_beta 66.9910(16) _cell_angle_gamma 80.8330(14) _cell_volume 700.67(4) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2557 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 282 _exptl_absorpt_coefficient_mu 0.828 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean . _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 5962 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0761 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4082 _reflns_number_gt 2681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0450P)^2^+0.0238P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4082 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0418 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.0000 1.0000 0.0000 0.02335(12) Uani 1 2 d S . . P1 P -0.02122(7) 0.84764(5) -0.09484(6) 0.02410(14) Uani 1 1 d . . . O1 O 0.10090(18) 0.84514(14) 0.12689(15) 0.0258(3) Uani 1 1 d . . . C1 C 0.2146(3) 0.6039(2) 0.2191(2) 0.0254(4) Uani 1 1 d . . . C2 C 0.1302(3) 0.7185(2) 0.1117(2) 0.0249(4) Uani 1 1 d . . . C3 C 0.0848(3) 0.6940(2) 0.0100(2) 0.0270(5) Uani 1 1 d . . . H3 H 0.1073 0.6043 -0.0035 0.032 Uiso 1 1 calc . . . C4 C 0.0892(3) 0.9036(2) -0.3084(2) 0.0349(5) Uani 1 1 d . . . H4 H 0.0183 0.9821 -0.3633 0.042 Uiso 1 1 calc . . . C5 C -0.2430(3) 0.7864(2) -0.0416(3) 0.0357(5) Uani 1 1 d . . . H5 H -0.2359 0.6929 -0.0554 0.043 Uiso 1 1 calc . . . C6 C 0.2656(3) 0.9730(3) -0.3618(3) 0.0513(7) Uani 1 1 d . . . H6A H 0.3319 0.9029 -0.2988 0.077 Uiso 1 1 calc . . . H6B H 0.2489 1.0650 -0.3471 0.077 Uiso 1 1 calc . . . H6C H 0.3295 0.9959 -0.4738 0.077 Uiso 1 1 calc . . . C7 C 0.1053(4) 0.7755(3) -0.3539(3) 0.0573(7) Uani 1 1 d . . . H7A H 0.1691 0.8099 -0.4679 0.086 Uiso 1 1 calc . . . H7B H -0.0110 0.7400 -0.3267 0.086 Uiso 1 1 calc . . . H7C H 0.1681 0.6940 -0.2963 0.086 Uiso 1 1 calc . . . C8 C -0.3427(3) 0.7524(3) 0.1323(3) 0.0561(8) Uani 1 1 d . . . H8A H -0.3408 0.8408 0.1492 0.084 Uiso 1 1 calc . . . H8B H -0.2880 0.6697 0.1976 0.084 Uiso 1 1 calc . . . H8C H -0.4633 0.7249 0.1619 0.084 Uiso 1 1 calc . . . C9 C -0.3365(3) 0.9035(3) -0.1452(3) 0.0479(7) Uani 1 1 d . . . H9A H -0.4569 0.8706 -0.1072 0.072 Uiso 1 1 calc . . . H9B H -0.2770 0.9167 -0.2550 0.072 Uiso 1 1 calc . . . H9C H -0.3355 0.9984 -0.1399 0.072 Uiso 1 1 calc . . . C10 C 0.3206(3) 0.4969(2) 0.1783(3) 0.0379(6) Uani 1 1 d . . . H10 H 0.3385 0.4944 0.0810 0.045 Uiso 1 1 calc . . . C11 C 0.4013(4) 0.3931(3) 0.2788(3) 0.0504(7) Uani 1 1 d . . . H11 H 0.4748 0.3208 0.2492 0.061 Uiso 1 1 calc . . . C12 C 0.3747(4) 0.3948(3) 0.4207(3) 0.0463(7) Uani 1 1 d . . . H12 H 0.4290 0.3234 0.4895 0.056 Uiso 1 1 calc . . . C13 C 0.2698(3) 0.4998(3) 0.4623(3) 0.0411(6) Uani 1 1 d . . . H13 H 0.2518 0.5009 0.5602 0.049 Uiso 1 1 calc . . . C14 C 0.1892(3) 0.6046(2) 0.3629(2) 0.0341(5) Uani 1 1 d . . . H14 H 0.1168 0.6770 0.3931 0.041 Uiso 1 1 calc . . . 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 Ni1 0.0277(2) 0.01876(19) 0.0282(2) -0.00967(15) -0.01566(16) 0.00225(15) P1 0.0294(3) 0.0201(3) 0.0289(3) -0.0110(2) -0.0169(2) 0.0033(2) O1 0.0352(8) 0.0195(7) 0.0312(7) -0.0119(6) -0.0207(6) 0.0051(6) C1 0.0264(10) 0.0187(9) 0.0326(10) -0.0078(8) -0.0153(9) -0.0012(8) C2 0.0240(10) 0.0201(10) 0.0287(10) -0.0078(8) -0.0104(8) -0.0002(8) C3 0.0367(12) 0.0179(9) 0.0353(11) -0.0140(9) -0.0213(10) 0.0080(8) C4 0.0406(13) 0.0350(12) 0.0298(11) -0.0113(10) -0.0183(10) 0.0062(10) C5 0.0354(12) 0.0333(12) 0.0459(13) -0.0168(10) -0.0213(11) -0.0015(10) C6 0.0476(16) 0.0560(16) 0.0368(13) -0.0123(12) -0.0082(12) -0.0053(13) C7 0.076(2) 0.0616(17) 0.0475(15) -0.0364(14) -0.0227(15) 0.0083(16) C8 0.0378(14) 0.0717(19) 0.0437(14) -0.0056(13) -0.0152(12) -0.0175(14) C9 0.0403(14) 0.0568(16) 0.0538(15) -0.0204(13) -0.0299(12) 0.0066(12) C10 0.0494(14) 0.0308(12) 0.0498(13) -0.0225(11) -0.0319(12) 0.0118(11) C11 0.0623(18) 0.0334(13) 0.0765(18) -0.0289(13) -0.0474(16) 0.0233(12) C12 0.0587(16) 0.0284(12) 0.0569(15) -0.0053(11) -0.0425(14) 0.0043(12) C13 0.0503(15) 0.0393(13) 0.0335(12) -0.0076(11) -0.0247(11) 0.0026(12) C14 0.0353(12) 0.0321(12) 0.0335(11) -0.0112(10) -0.0161(10) 0.0053(10) _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 Ni1 O1 1.8504(12) . ? Ni1 O1 1.8505(12) 2_575 ? Ni1 P1 2.1996(5) . ? Ni1 P1 2.1996(5) 2_575 ? P1 C3 1.7687(18) . ? P1 C4 1.836(2) . ? P1 C5 1.841(2) . ? O1 C2 1.322(2) . ? C1 C10 1.385(3) . ? C1 C14 1.393(3) . ? C1 C2 1.493(2) . ? C2 C3 1.354(3) . ? C3 H3 0.9500 . ? C4 C7 1.521(4) . ? C4 C6 1.523(3) . ? C4 H4 1.0000 . ? C5 C8 1.525(4) . ? C5 C9 1.530(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.393(3) . ? C10 H10 0.9500 . ? C11 C12 1.376(4) . ? C11 H11 0.9500 . ? C12 C13 1.369(4) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? 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 O1 Ni1 O1 179.998(1) . 2_575 ? O1 Ni1 P1 87.01(4) . . ? O1 Ni1 P1 92.99(4) 2_575 . ? O1 Ni1 P1 92.99(4) . 2_575 ? O1 Ni1 P1 87.01(4) 2_575 2_575 ? P1 Ni1 P1 180.0 . 2_575 ? C3 P1 C4 109.82(10) . . ? C3 P1 C5 107.90(9) . . ? C4 P1 C5 106.95(10) . . ? C3 P1 Ni1 97.94(7) . . ? C4 P1 Ni1 117.52(8) . . ? C5 P1 Ni1 115.99(8) . . ? C2 O1 Ni1 119.39(12) . . ? C10 C1 C14 118.72(18) . . ? C10 C1 C2 121.47(18) . . ? C14 C1 C2 119.81(19) . . ? O1 C2 C3 123.04(17) . . ? O1 C2 C1 113.96(17) . . ? C3 C2 C1 122.99(18) . . ? C2 C3 P1 112.44(15) . . ? C2 C3 H3 123.8 . . ? P1 C3 H3 123.8 . . ? C7 C4 C6 111.9(2) . . ? C7 C4 P1 112.66(15) . . ? C6 C4 P1 108.85(15) . . ? C7 C4 H4 107.7 . . ? C6 C4 H4 107.7 . . ? P1 C4 H4 107.7 . . ? C8 C5 C9 110.7(2) . . ? C8 C5 P1 107.99(14) . . ? C9 C5 P1 112.08(14) . . ? C8 C5 H5 108.7 . . ? C9 C5 H5 108.7 . . ? P1 C5 H5 108.7 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C8 H8A 109.5 . . ? C5 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C5 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 C11 120.5(2) . . ? C1 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 120.2(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C13 C12 C11 119.7(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.8(2) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C13 C14 C1 120.1(2) . . ? C13 C14 H14 120.0 . . ? C1 C14 H14 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Ni1 P1 C3 -3.34(8) . . . . ? O1 Ni1 P1 C3 176.66(8) 2_575 . . . ? P1 Ni1 P1 C3 -148(8) 2_575 . . . ? O1 Ni1 P1 C4 -120.65(9) . . . . ? O1 Ni1 P1 C4 59.35(9) 2_575 . . . ? P1 Ni1 P1 C4 95(8) 2_575 . . . ? O1 Ni1 P1 C5 111.06(9) . . . . ? O1 Ni1 P1 C5 -68.93(9) 2_575 . . . ? P1 Ni1 P1 C5 -33(8) 2_575 . . . ? O1 Ni1 O1 C2 153(4) 2_575 . . . ? P1 Ni1 O1 C2 3.52(14) . . . . ? P1 Ni1 O1 C2 -176.48(14) 2_575 . . . ? Ni1 O1 C2 C3 -2.1(3) . . . . ? Ni1 O1 C2 C1 179.07(11) . . . . ? C10 C1 C2 O1 -151.5(2) . . . . ? C14 C1 C2 O1 27.6(3) . . . . ? C10 C1 C2 C3 29.7(3) . . . . ? C14 C1 C2 C3 -151.2(2) . . . . ? O1 C2 C3 P1 -1.3(3) . . . . ? C1 C2 C3 P1 177.35(14) . . . . ? C4 P1 C3 C2 126.37(16) . . . . ? C5 P1 C3 C2 -117.39(17) . . . . ? Ni1 P1 C3 C2 3.27(16) . . . . ? C3 P1 C4 C7 54.6(2) . . . . ? C5 P1 C4 C7 -62.20(19) . . . . ? Ni1 P1 C4 C7 165.33(15) . . . . ? C3 P1 C4 C6 -70.08(19) . . . . ? C5 P1 C4 C6 173.09(16) . . . . ? Ni1 P1 C4 C6 40.61(19) . . . . ? C3 P1 C5 C8 66.83(19) . . . . ? C4 P1 C5 C8 -175.07(17) . . . . ? Ni1 P1 C5 C8 -41.77(19) . . . . ? C3 P1 C5 C9 -170.99(17) . . . . ? C4 P1 C5 C9 -52.9(2) . . . . ? Ni1 P1 C5 C9 80.41(18) . . . . ? C14 C1 C10 C11 -0.5(3) . . . . ? C2 C1 C10 C11 178.55(19) . . . . ? C1 C10 C11 C12 0.7(4) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C14 0.1(4) . . . . ? C12 C13 C14 C1 0.0(3) . . . . ? C10 C1 C14 C13 0.1(3) . . . . ? C2 C1 C14 C13 -178.93(18) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.03 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.501 _refine_diff_density_min -0.562 _refine_diff_density_rms 0.076 # Attachment 'Complex6.cif' data_Complex6 _database_code_depnum_ccdc_archive 'CCDC 698958' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H34 N2 Ni O2 P2' _chemical_formula_sum 'C16 H34 N2 Ni O2 P2' _chemical_formula_weight 407.10 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 12.4880(9) _cell_length_b 9.9680(7) _cell_length_c 17.9220(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.706(3) _cell_angle_gamma 90.00 _cell_volume 2113.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 12665 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 30.034 _exptl_crystal_description prism _exptl_crystal_colour orange _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.280 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 1.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4974 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0432 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2097 _reflns_number_gt 1899 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0537P)^2^+0.9620P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2097 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.1065 _refine_ls_wR_factor_gt 0.1027 _refine_ls_goodness_of_fit_ref 1.198 _refine_ls_restrained_S_all 1.198 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 1.0000 0.10530(4) 0.7500 0.03248(16) Uani 1 2 d S . . P1 P 0.88155(5) 0.23146(6) 0.66272(3) 0.03404(18) Uani 1 1 d . . . O1 O 0.92629(15) -0.03411(16) 0.68147(9) 0.0459(4) Uani 1 1 d . . . N1 N 0.81245(19) 0.1177(2) 0.59434(12) 0.0457(5) Uani 1 1 d . . . C1 C 0.8499(2) -0.0028(2) 0.61599(13) 0.0419(5) Uani 1 1 d . . . C2 C 0.8054(3) -0.1187(3) 0.56125(17) 0.0583(7) Uani 1 1 d . . . H2A H 0.8638 -0.1495 0.5395 0.088 Uiso 1 1 calc . . . H2B H 0.7386 -0.0901 0.5182 0.088 Uiso 1 1 calc . . . H2C H 0.7847 -0.1922 0.5903 0.088 Uiso 1 1 calc . . . C3 C 0.9210(2) 0.3556(3) 0.60089(14) 0.0467(6) Uani 1 1 d . . . H3 H 0.8537 0.3690 0.5529 0.056 Uiso 1 1 calc . . . C4 C 0.9528(3) 0.4931(3) 0.63950(17) 0.0661(8) Uani 1 1 d . . . H4A H 1.0219 0.4851 0.6848 0.099 Uiso 1 1 calc . . . H4B H 0.8911 0.5262 0.6573 0.099 Uiso 1 1 calc . . . H4C H 0.9656 0.5560 0.6012 0.099 Uiso 1 1 calc . . . C5 C 1.0153(3) 0.2977(4) 0.57319(18) 0.0757(10) Uani 1 1 d . . . H5A H 1.0271 0.3559 0.5324 0.114 Uiso 1 1 calc . . . H5B H 0.9939 0.2077 0.5515 0.114 Uiso 1 1 calc . . . H5C H 1.0854 0.2923 0.6179 0.114 Uiso 1 1 calc . . . C6 C 0.7704(2) 0.3095(2) 0.69516(14) 0.0436(5) Uani 1 1 d . . . H6 H 0.8056 0.3825 0.7334 0.052 Uiso 1 1 calc . . . C7 C 0.7228(3) 0.2037(3) 0.73804(18) 0.0641(8) Uani 1 1 d . . . H7A H 0.6670 0.2454 0.7586 0.096 Uiso 1 1 calc . . . H7B H 0.7844 0.1660 0.7817 0.096 Uiso 1 1 calc . . . H7C H 0.6866 0.1320 0.7012 0.096 Uiso 1 1 calc . . . C8 C 0.6760(3) 0.3705(4) 0.6274(2) 0.0707(9) Uani 1 1 d . . . H8A H 0.6437 0.3015 0.5876 0.106 Uiso 1 1 calc . . . H8B H 0.7066 0.4436 0.6037 0.106 Uiso 1 1 calc . . . H8C H 0.6170 0.4058 0.6472 0.106 Uiso 1 1 calc . . . 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 Ni1 0.0331(2) 0.0304(2) 0.0312(2) 0.000 0.00642(16) 0.000 P1 0.0346(3) 0.0339(3) 0.0301(3) -0.0012(2) 0.0055(2) -0.0001(2) O1 0.0507(10) 0.0342(8) 0.0452(9) -0.0055(7) 0.0046(8) -0.0021(8) N1 0.0492(12) 0.0435(11) 0.0359(10) -0.0088(8) 0.0019(9) -0.0002(9) C1 0.0412(12) 0.0434(13) 0.0407(12) -0.0106(10) 0.0126(10) -0.0057(11) C2 0.0631(18) 0.0504(15) 0.0539(16) -0.0186(12) 0.0081(13) -0.0070(13) C3 0.0443(13) 0.0555(14) 0.0354(11) 0.0109(11) 0.0058(10) -0.0025(12) C4 0.077(2) 0.0552(16) 0.0571(16) 0.0117(13) 0.0089(15) -0.0219(15) C5 0.0603(18) 0.118(3) 0.0560(17) 0.0229(19) 0.0291(15) 0.007(2) C6 0.0389(12) 0.0465(13) 0.0438(12) -0.0061(10) 0.0110(10) 0.0021(11) C7 0.0555(17) 0.075(2) 0.0686(18) -0.0041(15) 0.0294(15) -0.0134(16) C8 0.0498(17) 0.090(2) 0.0662(19) 0.0039(16) 0.0100(14) 0.0257(16) _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 Ni1 O1 1.8873(16) . ? Ni1 O1 1.8873(16) 2_756 ? Ni1 P1 2.1754(6) 2_756 ? Ni1 P1 2.1754(6) . ? P1 N1 1.690(2) . ? P1 C3 1.831(2) . ? P1 C6 1.841(2) . ? O1 C1 1.291(3) . ? N1 C1 1.302(3) . ? C1 C2 1.502(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.529(4) . ? C3 C5 1.531(4) . ? C3 H3 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C8 1.522(4) . ? C6 C7 1.532(4) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 O1 Ni1 O1 85.16(10) . 2_756 ? O1 Ni1 P1 166.14(5) . 2_756 ? O1 Ni1 P1 83.13(5) 2_756 2_756 ? O1 Ni1 P1 83.13(5) . . ? O1 Ni1 P1 166.14(6) 2_756 . ? P1 Ni1 P1 109.37(3) 2_756 . ? N1 P1 C3 100.89(11) . . ? N1 P1 C6 104.55(11) . . ? C3 P1 C6 106.40(12) . . ? N1 P1 Ni1 101.81(8) . . ? C3 P1 Ni1 124.95(8) . . ? C6 P1 Ni1 115.15(8) . . ? C1 O1 Ni1 118.54(15) . . ? C1 N1 P1 110.61(17) . . ? O1 C1 N1 125.7(2) . . ? O1 C1 C2 114.8(2) . . ? N1 C1 C2 119.5(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C5 111.8(3) . . ? C4 C3 P1 114.38(17) . . ? C5 C3 P1 109.0(2) . . ? C4 C3 H3 107.1 . . ? C5 C3 H3 107.1 . . ? P1 C3 H3 107.1 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C8 C6 C7 110.5(2) . . ? C8 C6 P1 112.70(18) . . ? C7 C6 P1 108.70(18) . . ? C8 C6 H6 108.3 . . ? C7 C6 H6 108.3 . . ? P1 C6 H6 108.3 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Ni1 P1 N1 -2.43(9) . . . . ? O1 Ni1 P1 N1 -35.0(2) 2_756 . . . ? P1 Ni1 P1 N1 171.41(9) 2_756 . . . ? O1 Ni1 P1 C3 -114.87(12) . . . . ? O1 Ni1 P1 C3 -147.4(2) 2_756 . . . ? P1 Ni1 P1 C3 58.97(11) 2_756 . . . ? O1 Ni1 P1 C6 110.01(10) . . . . ? O1 Ni1 P1 C6 77.4(2) 2_756 . . . ? P1 Ni1 P1 C6 -76.15(9) 2_756 . . . ? O1 Ni1 O1 C1 176.6(2) 2_756 . . . ? P1 Ni1 O1 C1 -150.98(18) 2_756 . . . ? P1 Ni1 O1 C1 4.02(16) . . . . ? C3 P1 N1 C1 130.46(19) . . . . ? C6 P1 N1 C1 -119.24(19) . . . . ? Ni1 P1 N1 C1 0.95(19) . . . . ? Ni1 O1 C1 N1 -5.0(3) . . . . ? Ni1 O1 C1 C2 173.35(18) . . . . ? P1 N1 C1 O1 2.3(3) . . . . ? P1 N1 C1 C2 -176.0(2) . . . . ? N1 P1 C3 C4 161.9(2) . . . . ? C6 P1 C3 C4 53.0(2) . . . . ? Ni1 P1 C3 C4 -85.3(2) . . . . ? N1 P1 C3 C5 -72.2(2) . . . . ? C6 P1 C3 C5 178.89(19) . . . . ? Ni1 P1 C3 C5 40.6(2) . . . . ? N1 P1 C6 C8 -56.6(2) . . . . ? C3 P1 C6 C8 49.7(2) . . . . ? Ni1 P1 C6 C8 -167.38(19) . . . . ? N1 P1 C6 C7 66.3(2) . . . . ? C3 P1 C6 C7 172.53(18) . . . . ? Ni1 P1 C6 C7 -44.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.472 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.188 # Attachment 'Complex7.cif' data_Complex7 _database_code_depnum_ccdc_archive 'CCDC 698959' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H26 N2 Ni O2 P2' _chemical_formula_sum 'C28 H26 N2 Ni O2 P2' _chemical_formula_weight 543.16 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ni Ni 0.3393 1.1124 '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/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.5110(8) _cell_length_b 8.9890(12) _cell_length_c 19.733(3) _cell_angle_alpha 90.000(7) _cell_angle_beta 112.010(9) _cell_angle_gamma 90.000(5) _cell_volume 2550.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2183 _cell_measurement_theta_min 1.018 _cell_measurement_theta_max 29.131 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.915 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5084 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 29.11 _reflns_number_total 3377 _reflns_number_gt 2742 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0401P)^2^+0.7388P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3377 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0576 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1110 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.139 _refine_ls_restrained_S_all 1.139 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni1 Ni 0.5000 0.41711(4) 0.2500 0.01995(12) Uani 1 2 d S . . P1 P 0.49053(3) 0.27166(6) 0.16081(3) 0.02112(14) Uani 1 1 d . . . O1 O 0.49245(10) 0.56877(15) 0.18159(8) 0.0265(3) Uani 1 1 d . . . N1 N 0.46810(13) 0.39210(19) 0.09076(9) 0.0255(4) Uani 1 1 d . . . C1 C 0.46838(17) 0.6548(2) 0.06237(12) 0.0351(5) Uani 1 1 d . . . H1A H 0.4056 0.6970 0.0464 0.053 Uiso 1 1 calc . . . H1B H 0.4797 0.6172 0.0198 0.053 Uiso 1 1 calc . . . H1C H 0.5142 0.7320 0.0867 0.053 Uiso 1 1 calc . . . C2 C 0.47698(14) 0.5298(2) 0.11466(11) 0.0246(4) Uani 1 1 d . . . C4 C 0.67594(14) 0.1743(2) 0.22284(12) 0.0292(5) Uani 1 1 d . . . H4 H 0.6798 0.2270 0.2656 0.035 Uiso 1 1 calc . . . C5 C 0.75368(15) 0.1015(3) 0.22034(14) 0.0356(5) Uani 1 1 d . . . H5 H 0.8105 0.1036 0.2616 0.043 Uiso 1 1 calc . . . C6 C 0.74872(16) 0.0261(3) 0.15811(15) 0.0401(6) Uani 1 1 d . . . H6 H 0.8022 -0.0230 0.1566 0.048 Uiso 1 1 calc . . . C7 C 0.66626(17) 0.0218(3) 0.09803(14) 0.0404(6) Uani 1 1 d . . . H7 H 0.6630 -0.0301 0.0552 0.048 Uiso 1 1 calc . . . C8 C 0.58833(16) 0.0931(2) 0.10024(13) 0.0336(5) Uani 1 1 d . . . H8 H 0.5316 0.0896 0.0589 0.040 Uiso 1 1 calc . . . C3 C 0.59258(14) 0.1701(2) 0.16271(11) 0.0244(4) Uani 1 1 d . . . C14 C 0.30827(14) 0.1748(2) 0.08897(11) 0.0280(5) Uani 1 1 d . . . H14 H 0.2954 0.2730 0.0700 0.034 Uiso 1 1 calc . . . C9 C 0.39925(13) 0.1338(2) 0.13192(11) 0.0237(4) Uani 1 1 d . . . C10 C 0.41696(15) -0.0117(2) 0.15763(11) 0.0282(5) Uani 1 1 d . . . H10 H 0.4789 -0.0420 0.1853 0.034 Uiso 1 1 calc . . . C11 C 0.34491(17) -0.1124(3) 0.14312(13) 0.0360(5) Uani 1 1 d . . . H11 H 0.3575 -0.2110 0.1616 0.043 Uiso 1 1 calc . . . C12 C 0.25470(17) -0.0705(3) 0.10186(14) 0.0384(6) Uani 1 1 d . . . H12 H 0.2052 -0.1395 0.0927 0.046 Uiso 1 1 calc . . . C13 C 0.23657(16) 0.0722(3) 0.07392(13) 0.0359(5) Uani 1 1 d . . . H13 H 0.1748 0.1002 0.0443 0.043 Uiso 1 1 calc . . . 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 Ni1 0.0213(2) 0.0186(2) 0.0198(2) 0.000 0.00755(15) 0.000 P1 0.0218(3) 0.0200(3) 0.0211(3) -0.00051(19) 0.0075(2) 0.0008(2) O1 0.0359(9) 0.0218(7) 0.0224(7) 0.0025(6) 0.0116(6) 0.0009(6) N1 0.0320(10) 0.0237(8) 0.0204(8) 0.0002(7) 0.0093(7) 0.0016(8) C1 0.0533(15) 0.0264(11) 0.0289(12) 0.0027(9) 0.0192(11) 0.0000(11) C2 0.0240(10) 0.0276(10) 0.0227(10) 0.0027(8) 0.0094(8) 0.0012(9) C4 0.0250(11) 0.0340(12) 0.0291(11) 0.0023(9) 0.0108(9) 0.0010(10) C5 0.0222(11) 0.0399(13) 0.0434(14) 0.0100(11) 0.0107(10) 0.0040(10) C6 0.0321(13) 0.0324(12) 0.0617(17) 0.0007(12) 0.0244(12) 0.0037(11) C7 0.0360(13) 0.0372(13) 0.0538(15) -0.0144(12) 0.0236(12) -0.0013(11) C8 0.0306(12) 0.0335(12) 0.0370(13) -0.0093(10) 0.0131(10) 0.0001(10) C3 0.0248(10) 0.0209(10) 0.0286(11) 0.0010(8) 0.0111(8) 0.0002(8) C14 0.0260(10) 0.0304(11) 0.0263(11) -0.0014(9) 0.0083(8) 0.0009(9) C9 0.0249(10) 0.0242(10) 0.0224(10) -0.0045(8) 0.0093(8) -0.0017(9) C10 0.0288(11) 0.0269(11) 0.0288(11) -0.0002(9) 0.0104(9) 0.0013(9) C11 0.0407(13) 0.0281(11) 0.0400(13) 0.0005(10) 0.0162(11) -0.0055(10) C12 0.0347(13) 0.0401(14) 0.0403(14) -0.0062(11) 0.0139(11) -0.0154(11) C13 0.0251(11) 0.0455(14) 0.0326(12) -0.0038(10) 0.0057(9) -0.0040(11) _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 Ni1 O1 1.8911(14) 2_655 ? Ni1 O1 1.8911(14) . ? Ni1 P1 2.1527(6) 2_655 ? Ni1 P1 2.1529(6) . ? P1 N1 1.6862(18) . ? P1 C9 1.805(2) . ? P1 C3 1.816(2) . ? O1 C2 1.299(2) . ? N1 C2 1.313(3) . ? C1 C2 1.497(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C4 C5 1.389(3) . ? C4 C3 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.379(4) . ? C5 H5 0.9500 . ? C6 C7 1.381(3) . ? C6 H6 0.9500 . ? C7 C8 1.383(3) . ? C7 H7 0.9500 . ? C8 C3 1.393(3) . ? C8 H8 0.9500 . ? C14 C13 1.388(3) . ? C14 C9 1.396(3) . ? C14 H14 0.9500 . ? C9 C10 1.393(3) . ? C10 C11 1.382(3) . ? C10 H10 0.9500 . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 O1 Ni1 O1 87.75(9) 2_655 . ? O1 Ni1 P1 83.52(5) 2_655 2_655 ? O1 Ni1 P1 171.27(5) . 2_655 ? O1 Ni1 P1 171.27(5) 2_655 . ? O1 Ni1 P1 83.52(5) . . ? P1 Ni1 P1 105.21(3) 2_655 . ? N1 P1 C9 106.58(9) . . ? N1 P1 C3 104.50(9) . . ? C9 P1 C3 103.64(9) . . ? N1 P1 Ni1 102.13(6) . . ? C9 P1 Ni1 118.69(7) . . ? C3 P1 Ni1 119.78(7) . . ? C2 O1 Ni1 118.03(13) . . ? C2 N1 P1 110.43(14) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 N1 125.02(18) . . ? O1 C2 C1 115.67(19) . . ? N1 C2 C1 119.31(19) . . ? C5 C4 C3 119.9(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 120.2(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C8 119.9(2) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C7 C8 C3 120.4(2) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? C4 C3 C8 119.30(19) . . ? C4 C3 P1 121.92(16) . . ? C8 C3 P1 118.66(16) . . ? C13 C14 C9 120.1(2) . . ? C13 C14 H14 120.0 . . ? C9 C14 H14 120.0 . . ? C10 C9 C14 119.03(19) . . ? C10 C9 P1 120.36(15) . . ? C14 C9 P1 120.35(16) . . ? C11 C10 C9 120.4(2) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.9(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.3(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Ni1 P1 N1 -8.6(3) 2_655 . . . ? O1 Ni1 P1 N1 -7.60(8) . . . . ? P1 Ni1 P1 N1 172.27(7) 2_655 . . . ? O1 Ni1 P1 C9 -125.4(3) 2_655 . . . ? O1 Ni1 P1 C9 -124.37(9) . . . . ? P1 Ni1 P1 C9 55.51(8) 2_655 . . . ? O1 Ni1 P1 C3 106.1(3) 2_655 . . . ? O1 Ni1 P1 C3 107.11(9) . . . . ? P1 Ni1 P1 C3 -73.02(8) 2_655 . . . ? O1 Ni1 O1 C2 -174.01(17) 2_655 . . . ? P1 Ni1 O1 C2 -173.1(2) 2_655 . . . ? P1 Ni1 O1 C2 6.14(14) . . . . ? C9 P1 N1 C2 134.09(15) . . . . ? C3 P1 N1 C2 -116.58(16) . . . . ? Ni1 P1 N1 C2 8.90(15) . . . . ? Ni1 O1 C2 N1 -1.6(3) . . . . ? Ni1 O1 C2 C1 177.93(14) . . . . ? P1 N1 C2 O1 -5.8(3) . . . . ? P1 N1 C2 C1 174.66(16) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 C8 -0.1(4) . . . . ? C6 C7 C8 C3 0.3(4) . . . . ? C5 C4 C3 C8 -0.4(3) . . . . ? C5 C4 C3 P1 -176.47(17) . . . . ? C7 C8 C3 C4 -0.1(3) . . . . ? C7 C8 C3 P1 176.12(19) . . . . ? N1 P1 C3 C4 118.33(18) . . . . ? C9 P1 C3 C4 -130.21(18) . . . . ? Ni1 P1 C3 C4 4.9(2) . . . . ? N1 P1 C3 C8 -57.76(19) . . . . ? C9 P1 C3 C8 53.71(19) . . . . ? Ni1 P1 C3 C8 -171.21(14) . . . . ? C13 C14 C9 C10 1.6(3) . . . . ? C13 C14 C9 P1 -172.60(18) . . . . ? N1 P1 C9 C10 149.07(17) . . . . ? C3 P1 C9 C10 39.13(19) . . . . ? Ni1 P1 C9 C10 -96.55(17) . . . . ? N1 P1 C9 C14 -36.80(19) . . . . ? C3 P1 C9 C14 -146.74(17) . . . . ? Ni1 P1 C9 C14 77.58(18) . . . . ? C14 C9 C10 C11 -2.4(3) . . . . ? P1 C9 C10 C11 171.76(18) . . . . ? C9 C10 C11 C12 1.1(4) . . . . ? C10 C11 C12 C13 1.1(4) . . . . ? C11 C12 C13 C14 -1.9(4) . . . . ? C9 C14 C13 C12 0.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 29.11 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.453 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.165 # Attachment 'HL3.cif' data_HL3 _database_code_depnum_ccdc_archive 'CCDC 698960' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C8 H18 N O P' _chemical_formula_sum 'C8 H18 N O P' _chemical_formula_weight 175.20 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 15.5860(5) _cell_length_b 7.8790(4) _cell_length_c 9.1420(12) _cell_angle_alpha 90.00 _cell_angle_beta 105.741(2) _cell_angle_gamma 90.00 _cell_volume 1080.55(16) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2373 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 29.131 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.077 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.209 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 KappaCCD _diffrn_measurement_method '\f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5114 _diffrn_reflns_av_R_equivalents 0.0466 _diffrn_reflns_av_sigmaI/netI 0.0861 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 29.15 _reflns_number_total 2898 _reflns_number_gt 1559 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Denzo (Nonius B.V., 1998)' _computing_data_reduction 'Denzo (Nonius B.V., 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON 98 (Spek, 1998)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0692P)^2^+0.0865P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2898 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1227 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1410 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.020 _refine_ls_shift/su_mean 0.001 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 0.73011(4) 0.14828(8) 0.82042(7) 0.0449(2) Uani 1 1 d . . . O O 0.88123(11) 0.3602(2) 0.98553(18) 0.0542(5) Uani 1 1 d . . . N N 0.81734(13) 0.2327(3) 0.7619(2) 0.0404(5) Uani 1 1 d . . . C1 C 0.95514(17) 0.3865(3) 0.7901(3) 0.0590(7) Uani 1 1 d . . . H1A H 1.0007 0.4449 0.8692 0.088 Uiso 1 1 calc . . . H1B H 0.9306 0.4651 0.7061 0.088 Uiso 1 1 calc . . . H1C H 0.9820 0.2891 0.7526 0.088 Uiso 1 1 calc . . . C2 C 0.88185(15) 0.3261(3) 0.8552(3) 0.0383(5) Uani 1 1 d . . . C3 C 0.63441(16) 0.2302(4) 0.6690(3) 0.0561(7) Uani 1 1 d . . . H3 H 0.6419 0.1945 0.5682 0.067 Uiso 1 1 calc . . . C4 C 0.63207(19) 0.4222(4) 0.6737(3) 0.0722(8) Uani 1 1 d . . . H4A H 0.5809 0.4638 0.5938 0.108 Uiso 1 1 calc . . . H4B H 0.6872 0.4679 0.6573 0.108 Uiso 1 1 calc . . . H4C H 0.6266 0.4593 0.7731 0.108 Uiso 1 1 calc . . . C5 C 0.5480(2) 0.1529(5) 0.6877(4) 0.0880(11) Uani 1 1 d . . . H5A H 0.5407 0.1838 0.7875 0.132 Uiso 1 1 calc . . . H5B H 0.5506 0.0290 0.6798 0.132 Uiso 1 1 calc . . . H5C H 0.4973 0.1963 0.6078 0.132 Uiso 1 1 calc . . . C6 C 0.7377(2) -0.0755(4) 0.7710(4) 0.0667(8) Uani 1 1 d . . . H6 H 0.6911 -0.1372 0.8067 0.080 Uiso 1 1 calc . . . C7 C 0.7216(3) -0.1183(4) 0.6030(4) 0.0986(13) Uani 1 1 d . . . H7A H 0.7663 -0.0610 0.5631 0.148 Uiso 1 1 calc . . . H7B H 0.6619 -0.0800 0.5469 0.148 Uiso 1 1 calc . . . H7C H 0.7262 -0.2413 0.5911 0.148 Uiso 1 1 calc . . . C8 C 0.8274(3) -0.1448(4) 0.8628(5) 0.1030(13) Uani 1 1 d . . . H8A H 0.8301 -0.2670 0.8444 0.154 Uiso 1 1 calc . . . H8B H 0.8343 -0.1248 0.9712 0.154 Uiso 1 1 calc . . . H8C H 0.8754 -0.0872 0.8318 0.154 Uiso 1 1 calc . . . H1 H 0.8215(15) 0.220(3) 0.688(3) 0.037(7) 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 P 0.0443(4) 0.0620(4) 0.0331(4) -0.0058(3) 0.0187(3) -0.0128(3) O 0.0582(11) 0.0725(11) 0.0340(9) -0.0132(8) 0.0162(8) -0.0218(8) N 0.0432(12) 0.0529(12) 0.0294(11) -0.0084(10) 0.0173(9) -0.0101(9) C1 0.0517(16) 0.0772(17) 0.0536(16) -0.0110(13) 0.0236(13) -0.0218(13) C2 0.0385(13) 0.0443(13) 0.0331(12) 0.0006(10) 0.0113(10) -0.0016(10) C3 0.0403(14) 0.092(2) 0.0365(13) -0.0063(13) 0.0116(11) -0.0138(13) C4 0.0628(19) 0.087(2) 0.068(2) 0.0033(17) 0.0210(16) 0.0227(15) C5 0.0463(18) 0.148(3) 0.069(2) -0.005(2) 0.0155(16) -0.0267(18) C6 0.083(2) 0.0571(16) 0.074(2) -0.0062(15) 0.0444(17) -0.0222(15) C7 0.166(4) 0.070(2) 0.084(3) -0.0237(17) 0.074(3) -0.037(2) C8 0.100(3) 0.067(2) 0.163(4) 0.026(2) 0.072(3) 0.0102(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P N 1.724(2) . ? P C6 1.832(3) . ? P C3 1.854(3) . ? O C2 1.224(3) . ? N C2 1.347(3) . ? N H1 0.70(2) . ? C1 C2 1.501(3) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C3 C4 1.514(4) . ? C3 C5 1.530(4) . ? C3 H3 1.0000 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C8 1.522(5) . ? C6 C7 1.525(4) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? 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 N P C6 100.68(11) . . ? N P C3 100.16(11) . . ? C6 P C3 104.11(14) . . ? C2 N P 122.06(16) . . ? C2 N H1 116(2) . . ? P N H1 122(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O C2 N 122.3(2) . . ? O C2 C1 121.6(2) . . ? N C2 C1 116.1(2) . . ? C4 C3 C5 111.5(2) . . ? C4 C3 P 110.32(18) . . ? C5 C3 P 109.4(2) . . ? C4 C3 H3 108.5 . . ? C5 C3 H3 108.5 . . ? P C3 H3 108.5 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C8 C6 C7 110.6(3) . . ? C8 C6 P 108.7(2) . . ? C7 C6 P 117.2(2) . . ? C8 C6 H6 106.6 . . ? C7 C6 H6 106.6 . . ? P C6 H6 106.6 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 P N C2 -126.6(2) . . . . ? C3 P N C2 126.8(2) . . . . ? P N C2 O -1.9(3) . . . . ? P N C2 C1 178.08(18) . . . . ? N P C3 C4 -63.59(19) . . . . ? C6 P C3 C4 -167.42(18) . . . . ? N P C3 C5 173.4(2) . . . . ? C6 P C3 C5 69.6(2) . . . . ? N P C6 C8 62.3(2) . . . . ? C3 P C6 C8 165.7(2) . . . . ? N P C6 C7 -64.0(3) . . . . ? C3 P C6 C7 39.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 29.15 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.320 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.051