# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Simon Duckett' _publ_contact_author_email SBD3@YORK.AC.UK _publ_section_title ; An NMR Study of cobalt-catalyzed hydroformylation using Para-Hydrogen Induced Polarisation ; loop_ _publ_author_name 'Simon Duckett' 'Cyril Godard' 'Stacey Polas' 'Robert P. Tooze' 'Adrian C. Whitwood' # Attachment 'sbd0401m.cif' data_sbd0401m _database_code_depnum_ccdc_archive 'CCDC 701811' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H29 Co O P2' _chemical_formula_sum 'C30 H29 Co O P2' _chemical_formula_weight 526.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Co Co 0.3494 0.9721 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.4425(7) _cell_length_b 9.4559(6) _cell_length_c 14.7071(10) _cell_angle_alpha 93.077(2) _cell_angle_beta 104.880(2) _cell_angle_gamma 101.761(2) _cell_volume 1234.65(15) _cell_formula_units_Z 2 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 2638 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 25.01 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 0.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.822 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7070 _diffrn_reflns_av_R_equivalents 0.0211 _diffrn_reflns_av_sigmaI/netI 0.0440 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.44 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4325 _reflns_number_gt 3560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.4169P] 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 4325 _refine_ls_number_parameters 307 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0461 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C5 C -0.0668(3) 0.4369(3) 0.74450(17) 0.0179(5) Uani 1 1 d . . . H5A H -0.1759 0.3935 0.7201 0.021 Uiso 1 1 calc R . . H5B H -0.0506 0.5049 0.8017 0.021 Uiso 1 1 calc R . . Co1 Co 0.22121(4) 0.31334(3) 0.71022(2) 0.01574(11) Uani 1 1 d . . . P2 P 0.19351(7) 0.53426(6) 0.69671(4) 0.01520(15) Uani 1 1 d . . . P1 P 0.03793(7) 0.29058(6) 0.77541(4) 0.01512(15) Uani 1 1 d . . . O1 O 0.1012(2) 0.1771(2) 0.51497(13) 0.0360(5) Uani 1 1 d . . . C30 C 0.3274(3) 0.5781(3) 0.54859(17) 0.0214(6) Uani 1 1 d . . . H30 H 0.3420 0.4821 0.5543 0.026 Uiso 1 1 calc R . . C25 C 0.2542(3) 0.6377(3) 0.60646(16) 0.0176(5) Uani 1 1 d . . . C10 C 0.2026(3) 0.3276(3) 1.10329(17) 0.0206(5) Uani 1 1 d . . . H10 H 0.2387 0.3348 1.1703 0.025 Uiso 1 1 calc R . . C12 C 0.1530(3) 0.4413(3) 0.95970(17) 0.0195(5) Uani 1 1 d . . . H12 H 0.1580 0.5273 0.9290 0.023 Uiso 1 1 calc R . . C24 C 0.1824(3) 0.7555(3) 0.83408(18) 0.0210(6) Uani 1 1 d . . . H24 H 0.0862 0.7589 0.7950 0.025 Uiso 1 1 calc R . . C20 C 0.4107(3) 0.6724(3) 0.85934(17) 0.0200(5) Uani 1 1 d . . . H20 H 0.4710 0.6160 0.8382 0.024 Uiso 1 1 calc R . . C18 C -0.2388(3) 0.1174(3) 0.78332(17) 0.0193(5) Uani 1 1 d . . . H18 H -0.2437 0.1973 0.8235 0.023 Uiso 1 1 calc R . . C17 C -0.3552(3) -0.0051(3) 0.76057(17) 0.0212(6) Uani 1 1 d . . . H17 H -0.4396 -0.0091 0.7850 0.025 Uiso 1 1 calc R . . C13 C -0.1137(3) 0.1248(2) 0.74773(16) 0.0170(5) Uani 1 1 d . . . C14 C -0.1076(3) 0.0062(3) 0.69021(17) 0.0203(5) Uani 1 1 d . . . H14 H -0.0227 0.0091 0.6664 0.024 Uiso 1 1 calc R . . C3 C 0.4070(3) 0.2967(3) 0.80584(18) 0.0221(6) Uani 1 1 d . . . H3 H 0.4396 0.3500 0.8669 0.027 Uiso 1 1 calc R . . C26 C 0.2319(3) 0.7785(3) 0.59571(18) 0.0235(6) Uani 1 1 d . . . H26 H 0.1813 0.8204 0.6344 0.028 Uiso 1 1 calc R . . C16 C -0.3485(3) -0.1217(3) 0.70215(18) 0.0229(6) Uani 1 1 d . . . H16 H -0.4290 -0.2055 0.6860 0.027 Uiso 1 1 calc R . . C11 C 0.2067(3) 0.4521(3) 1.05769(18) 0.0221(6) Uani 1 1 d . . . H11 H 0.2461 0.5450 1.0934 0.027 Uiso 1 1 calc R . . C22 C 0.3791(3) 0.8364(3) 0.97889(18) 0.0248(6) Uani 1 1 d . . . H22 H 0.4154 0.8904 1.0398 0.030 Uiso 1 1 calc R . . C15 C -0.2251(3) -0.1169(3) 0.66715(18) 0.0235(6) Uani 1 1 d . . . H15 H -0.2205 -0.1975 0.6274 0.028 Uiso 1 1 calc R . . C21 C 0.4681(3) 0.7568(3) 0.94655(18) 0.0241(6) Uani 1 1 d . . . H21 H 0.5674 0.7600 0.9837 0.029 Uiso 1 1 calc R . . C7 C 0.0923(3) 0.3068(3) 0.90589(17) 0.0165(5) Uani 1 1 d . . . C28 C 0.3577(3) 0.7964(3) 0.47247(18) 0.0270(6) Uani 1 1 d . . . H28 H 0.3935 0.8504 0.4271 0.032 Uiso 1 1 calc R . . C8 C 0.0901(3) 0.1823(3) 0.95298(18) 0.0216(6) Uani 1 1 d . . . H8 H 0.0500 0.0893 0.9176 0.026 Uiso 1 1 calc R . . C23 C 0.2373(3) 0.8372(3) 0.92237(18) 0.0237(6) Uani 1 1 d . . . H23 H 0.1774 0.8937 0.9439 0.028 Uiso 1 1 calc R . . C4 C 0.4521(3) 0.3511(3) 0.72731(18) 0.0222(6) Uani 1 1 d . . . H4A H 0.4171 0.2944 0.6673 0.027 Uiso 1 1 calc R . . H4B H 0.5174 0.4443 0.7346 0.027 Uiso 1 1 calc R . . C29 C 0.3795(3) 0.6579(3) 0.48228(18) 0.0251(6) Uani 1 1 d . . . H29 H 0.4304 0.6164 0.4436 0.030 Uiso 1 1 calc R . . C6 C -0.0106(3) 0.5189(3) 0.66914(17) 0.0176(5) Uani 1 1 d . . . H6A H -0.0329 0.6168 0.6698 0.021 Uiso 1 1 calc R . . H6B H -0.0611 0.4655 0.6055 0.021 Uiso 1 1 calc R . . C1 C 0.1475(3) 0.2293(3) 0.59225(19) 0.0218(6) Uani 1 1 d . . . C9 C 0.1457(3) 0.1926(3) 1.05067(18) 0.0224(6) Uani 1 1 d . . . H9 H 0.1447 0.1068 1.0815 0.027 Uiso 1 1 calc R . . C2 C 0.3100(3) 0.1570(3) 0.78643(19) 0.0244(6) Uani 1 1 d . . . H2A H 0.2799 0.1071 0.7244 0.029 Uiso 1 1 calc R . . H2B H 0.2747 0.1131 0.8355 0.029 Uiso 1 1 calc R . . C27 C 0.2829(3) 0.8573(3) 0.52926(19) 0.0286(6) Uani 1 1 d . . . H27 H 0.2670 0.9526 0.5224 0.034 Uiso 1 1 calc R . . C19 C 0.2669(3) 0.6687(2) 0.80213(16) 0.0165(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C5 0.0170(13) 0.0184(12) 0.0190(12) 0.0014(10) 0.0052(10) 0.0052(10) Co1 0.01666(19) 0.01651(18) 0.01528(18) 0.00244(13) 0.00574(14) 0.00461(13) P2 0.0161(3) 0.0166(3) 0.0134(3) 0.0030(2) 0.0046(3) 0.0037(3) P1 0.0162(3) 0.0149(3) 0.0149(3) 0.0018(2) 0.0053(3) 0.0036(3) O1 0.0375(12) 0.0452(12) 0.0215(11) -0.0094(9) 0.0067(9) 0.0058(10) C30 0.0193(14) 0.0259(13) 0.0173(12) 0.0040(10) 0.0030(11) 0.0035(11) C25 0.0145(12) 0.0219(13) 0.0137(12) 0.0045(10) 0.0013(10) 0.0007(10) C10 0.0184(13) 0.0308(14) 0.0136(12) 0.0059(11) 0.0046(10) 0.0065(11) C12 0.0239(14) 0.0174(12) 0.0185(12) 0.0037(10) 0.0075(11) 0.0051(11) C24 0.0226(14) 0.0161(12) 0.0250(14) 0.0064(10) 0.0075(11) 0.0040(11) C20 0.0213(14) 0.0216(13) 0.0180(12) 0.0021(10) 0.0087(11) 0.0028(11) C18 0.0216(13) 0.0199(12) 0.0177(12) 0.0037(10) 0.0067(11) 0.0060(11) C17 0.0176(13) 0.0255(14) 0.0210(13) 0.0074(11) 0.0054(11) 0.0049(11) C13 0.0192(13) 0.0164(12) 0.0140(12) 0.0039(9) 0.0035(10) 0.0020(10) C14 0.0240(14) 0.0190(13) 0.0186(12) 0.0021(10) 0.0079(11) 0.0040(11) C3 0.0195(14) 0.0279(14) 0.0210(13) 0.0062(11) 0.0043(11) 0.0105(11) C26 0.0258(15) 0.0258(14) 0.0205(13) 0.0054(11) 0.0068(11) 0.0081(12) C16 0.0211(14) 0.0206(13) 0.0211(13) 0.0053(10) 0.0002(11) -0.0019(11) C11 0.0244(14) 0.0230(13) 0.0199(13) -0.0016(10) 0.0082(11) 0.0057(11) C22 0.0326(16) 0.0191(13) 0.0198(13) -0.0026(11) 0.0096(12) -0.0029(12) C15 0.0310(15) 0.0201(13) 0.0175(13) 0.0004(10) 0.0049(12) 0.0044(11) C21 0.0206(14) 0.0273(14) 0.0201(13) 0.0012(11) 0.0040(11) -0.0022(11) C7 0.0150(12) 0.0198(12) 0.0168(12) 0.0030(10) 0.0064(10) 0.0055(10) C28 0.0251(15) 0.0364(16) 0.0179(13) 0.0123(11) 0.0060(11) 0.0007(12) C8 0.0192(13) 0.0197(13) 0.0259(14) 0.0036(11) 0.0056(11) 0.0048(11) C23 0.0302(15) 0.0149(12) 0.0293(14) -0.0002(11) 0.0139(13) 0.0059(11) C4 0.0169(13) 0.0277(14) 0.0222(13) 0.0024(11) 0.0053(11) 0.0058(11) C29 0.0228(14) 0.0373(16) 0.0157(13) 0.0042(11) 0.0078(11) 0.0044(12) C6 0.0153(13) 0.0201(12) 0.0166(12) 0.0034(10) 0.0018(10) 0.0052(10) C1 0.0211(14) 0.0234(13) 0.0251(15) 0.0024(11) 0.0111(12) 0.0084(11) C9 0.0190(13) 0.0246(13) 0.0253(14) 0.0125(11) 0.0066(11) 0.0053(11) C2 0.0255(15) 0.0283(14) 0.0245(14) 0.0115(11) 0.0089(12) 0.0126(12) C27 0.0331(16) 0.0268(14) 0.0278(15) 0.0121(12) 0.0088(13) 0.0080(12) C19 0.0214(13) 0.0143(12) 0.0147(12) 0.0046(9) 0.0069(10) 0.0030(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 C5 C6 1.529(3) . ? C5 P1 1.869(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? Co1 C1 1.770(3) . ? Co1 C3 1.987(3) . ? Co1 C4 2.082(3) . ? Co1 C2 2.084(3) . ? Co1 P1 2.1640(7) . ? Co1 P2 2.1709(7) . ? P2 C25 1.830(2) . ? P2 C19 1.838(2) . ? P2 C6 1.838(2) . ? P1 C13 1.841(2) . ? P1 C7 1.844(2) . ? O1 C1 1.150(3) . ? C30 C25 1.389(4) . ? C30 C29 1.392(3) . ? C30 H30 0.9500 . ? C25 C26 1.401(3) . ? C10 C11 1.384(4) . ? C10 C9 1.385(4) . ? C10 H10 0.9500 . ? C12 C11 1.390(3) . ? C12 C7 1.391(3) . ? C12 H12 0.9500 . ? C24 C23 1.391(4) . ? C24 C19 1.396(3) . ? C24 H24 0.9500 . ? C20 C21 1.390(4) . ? C20 C19 1.395(4) . ? C20 H20 0.9500 . ? C18 C17 1.382(4) . ? C18 C13 1.401(3) . ? C18 H18 0.9500 . ? C17 C16 1.383(4) . ? C17 H17 0.9500 . ? C13 C14 1.388(3) . ? C14 C15 1.393(4) . ? C14 H14 0.9500 . ? C3 C2 1.413(4) . ? C3 C4 1.417(4) . ? C3 H3 0.9500 . ? C26 C27 1.384(4) . ? C26 H26 0.9500 . ? C16 C15 1.383(4) . ? C16 H16 0.9500 . ? C11 H11 0.9500 . ? C22 C23 1.385(4) . ? C22 C21 1.387(4) . ? C22 H22 0.9500 . ? C15 H15 0.9500 . ? C21 H21 0.9500 . ? C7 C8 1.396(3) . ? C28 C29 1.376(4) . ? C28 C27 1.395(4) . ? C28 H28 0.9500 . ? C8 C9 1.388(4) . ? C8 H8 0.9500 . ? C23 H23 0.9500 . ? C4 H4A 0.9500 . ? C4 H4B 0.9500 . ? C29 H29 0.9500 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C9 H9 0.9500 . ? C2 H2A 0.9500 . ? C2 H2B 0.9500 . ? C27 H27 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 C6 C5 P1 109.25(16) . . ? C6 C5 H5A 109.8 . . ? P1 C5 H5A 109.8 . . ? C6 C5 H5B 109.8 . . ? P1 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? C1 Co1 C3 128.64(11) . . ? C1 Co1 C4 102.12(11) . . ? C3 Co1 C4 40.66(10) . . ? C1 Co1 C2 104.84(11) . . ? C3 Co1 C2 40.53(10) . . ? C4 Co1 C2 69.86(10) . . ? C1 Co1 P1 107.89(9) . . ? C3 Co1 P1 109.22(8) . . ? C4 Co1 P1 148.17(7) . . ? C2 Co1 P1 92.05(8) . . ? C1 Co1 P2 102.69(8) . . ? C3 Co1 P2 114.63(8) . . ? C4 Co1 P2 98.66(7) . . ? C2 Co1 P2 151.84(8) . . ? P1 Co1 P2 85.06(3) . . ? C25 P2 C19 101.80(11) . . ? C25 P2 C6 105.39(11) . . ? C19 P2 C6 102.81(11) . . ? C25 P2 Co1 121.32(8) . . ? C19 P2 Co1 118.73(8) . . ? C6 P2 Co1 104.71(8) . . ? C13 P1 C7 100.58(11) . . ? C13 P1 C5 102.73(11) . . ? C7 P1 C5 104.69(11) . . ? C13 P1 Co1 121.08(8) . . ? C7 P1 Co1 115.78(8) . . ? C5 P1 Co1 110.06(8) . . ? C25 C30 C29 120.5(2) . . ? C25 C30 H30 119.7 . . ? C29 C30 H30 119.7 . . ? C30 C25 C26 118.7(2) . . ? C30 C25 P2 119.92(19) . . ? C26 C25 P2 121.34(19) . . ? C11 C10 C9 119.6(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C11 C12 C7 121.1(2) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? C23 C24 C19 120.9(2) . . ? C23 C24 H24 119.6 . . ? C19 C24 H24 119.6 . . ? C21 C20 C19 121.6(2) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C17 C18 C13 120.7(2) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C18 C17 C16 119.9(2) . . ? C18 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C14 C13 C18 118.8(2) . . ? C14 C13 P1 120.85(19) . . ? C18 C13 P1 120.32(18) . . ? C13 C14 C15 120.5(2) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C2 C3 C4 114.9(2) . . ? C2 C3 Co1 73.41(15) . . ? C4 C3 Co1 73.27(15) . . ? C2 C3 H3 122.5 . . ? C4 C3 H3 122.5 . . ? Co1 C3 H3 122.2 . . ? C27 C26 C25 120.7(2) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C15 C16 C17 120.2(2) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C10 C11 C12 120.1(2) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C23 C22 C21 120.0(2) . . ? C23 C22 H22 120.0 . . ? C21 C22 H22 120.0 . . ? C16 C15 C14 119.9(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C22 C21 C20 119.4(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C12 C7 C8 118.0(2) . . ? C12 C7 P1 121.30(18) . . ? C8 C7 P1 120.24(18) . . ? C29 C28 C27 119.9(2) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C22 C23 C24 120.1(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C3 C4 Co1 66.07(14) . . ? C3 C4 H4A 120.0 . . ? Co1 C4 H4A 80.3 . . ? C3 C4 H4B 120.0 . . ? Co1 C4 H4B 125.0 . . ? H4A C4 H4B 120.0 . . ? C28 C29 C30 120.4(2) . . ? C28 C29 H29 119.8 . . ? C30 C29 H29 119.8 . . ? C5 C6 P2 107.59(16) . . ? C5 C6 H6A 110.2 . . ? P2 C6 H6A 110.2 . . ? C5 C6 H6B 110.2 . . ? P2 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? O1 C1 Co1 178.6(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C3 C2 Co1 66.06(14) . . ? C3 C2 H2A 120.0 . . ? Co1 C2 H2A 80.3 . . ? C3 C2 H2B 120.0 . . ? Co1 C2 H2B 125.1 . . ? H2A C2 H2B 120.0 . . ? C26 C27 C28 119.8(3) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C20 C19 C24 117.9(2) . . ? C20 C19 P2 117.49(18) . . ? C24 C19 P2 124.26(19) . . ? 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 C1 Co1 P2 C25 -48.70(13) . . . . ? C3 Co1 P2 C25 95.14(12) . . . . ? C4 Co1 P2 C25 55.89(12) . . . . ? C2 Co1 P2 C25 118.93(18) . . . . ? P1 Co1 P2 C25 -155.96(9) . . . . ? C1 Co1 P2 C19 -176.04(12) . . . . ? C3 Co1 P2 C19 -32.20(13) . . . . ? C4 Co1 P2 C19 -71.45(12) . . . . ? C2 Co1 P2 C19 -8.41(19) . . . . ? P1 Co1 P2 C19 76.70(9) . . . . ? C1 Co1 P2 C6 70.05(12) . . . . ? C3 Co1 P2 C6 -146.11(11) . . . . ? C4 Co1 P2 C6 174.64(11) . . . . ? C2 Co1 P2 C6 -122.32(18) . . . . ? P1 Co1 P2 C6 -37.21(8) . . . . ? C6 C5 P1 C13 -121.44(17) . . . . ? C6 C5 P1 C7 133.85(17) . . . . ? C6 C5 P1 Co1 8.80(18) . . . . ? C1 Co1 P1 C13 36.43(12) . . . . ? C3 Co1 P1 C13 -107.42(12) . . . . ? C4 Co1 P1 C13 -123.34(16) . . . . ? C2 Co1 P1 C13 -69.88(12) . . . . ? P2 Co1 P1 C13 138.19(9) . . . . ? C1 Co1 P1 C7 158.38(12) . . . . ? C3 Co1 P1 C7 14.54(12) . . . . ? C4 Co1 P1 C7 -1.39(17) . . . . ? C2 Co1 P1 C7 52.07(12) . . . . ? P2 Co1 P1 C7 -99.86(9) . . . . ? C1 Co1 P1 C5 -83.18(12) . . . . ? C3 Co1 P1 C5 132.97(12) . . . . ? C4 Co1 P1 C5 117.05(16) . . . . ? C2 Co1 P1 C5 170.51(11) . . . . ? P2 Co1 P1 C5 18.58(9) . . . . ? C29 C30 C25 C26 1.0(4) . . . . ? C29 C30 C25 P2 -177.38(19) . . . . ? C19 P2 C25 C30 130.8(2) . . . . ? C6 P2 C25 C30 -122.2(2) . . . . ? Co1 P2 C25 C30 -3.8(2) . . . . ? C19 P2 C25 C26 -47.5(2) . . . . ? C6 P2 C25 C26 59.5(2) . . . . ? Co1 P2 C25 C26 177.91(17) . . . . ? C13 C18 C17 C16 0.0(4) . . . . ? C17 C18 C13 C14 -0.9(4) . . . . ? C17 C18 C13 P1 178.08(18) . . . . ? C7 P1 C13 C14 -123.9(2) . . . . ? C5 P1 C13 C14 128.3(2) . . . . ? Co1 P1 C13 C14 5.1(2) . . . . ? C7 P1 C13 C18 57.2(2) . . . . ? C5 P1 C13 C18 -50.7(2) . . . . ? Co1 P1 C13 C18 -173.80(16) . . . . ? C18 C13 C14 C15 1.0(4) . . . . ? P1 C13 C14 C15 -177.90(18) . . . . ? C1 Co1 C3 C2 -64.5(2) . . . . ? C4 Co1 C3 C2 -123.3(2) . . . . ? P1 Co1 C3 C2 69.55(15) . . . . ? P2 Co1 C3 C2 162.96(13) . . . . ? C1 Co1 C3 C4 58.8(2) . . . . ? C2 Co1 C3 C4 123.3(2) . . . . ? P1 Co1 C3 C4 -167.17(13) . . . . ? P2 Co1 C3 C4 -73.75(16) . . . . ? C30 C25 C26 C27 -0.5(4) . . . . ? P2 C25 C26 C27 177.8(2) . . . . ? C18 C17 C16 C15 0.6(4) . . . . ? C9 C10 C11 C12 0.4(4) . . . . ? C7 C12 C11 C10 1.1(4) . . . . ? C17 C16 C15 C14 -0.5(4) . . . . ? C13 C14 C15 C16 -0.4(4) . . . . ? C23 C22 C21 C20 -3.3(4) . . . . ? C19 C20 C21 C22 1.7(4) . . . . ? C11 C12 C7 C8 -1.6(4) . . . . ? C11 C12 C7 P1 -174.0(2) . . . . ? C13 P1 C7 C12 -151.6(2) . . . . ? C5 P1 C7 C12 -45.3(2) . . . . ? Co1 P1 C7 C12 76.0(2) . . . . ? C13 P1 C7 C8 36.1(2) . . . . ? C5 P1 C7 C8 142.4(2) . . . . ? Co1 P1 C7 C8 -96.3(2) . . . . ? C12 C7 C8 C9 0.5(4) . . . . ? P1 C7 C8 C9 173.1(2) . . . . ? C21 C22 C23 C24 1.6(4) . . . . ? C19 C24 C23 C22 1.8(4) . . . . ? C2 C3 C4 Co1 62.07(19) . . . . ? C1 Co1 C4 C3 -136.90(16) . . . . ? C2 Co1 C4 C3 -35.35(16) . . . . ? P1 Co1 C4 C3 23.4(2) . . . . ? P2 Co1 C4 C3 118.03(14) . . . . ? C27 C28 C29 C30 0.0(4) . . . . ? C25 C30 C29 C28 -0.7(4) . . . . ? P1 C5 C6 P2 -37.7(2) . . . . ? C25 P2 C6 C5 -178.36(16) . . . . ? C19 P2 C6 C5 -72.09(18) . . . . ? Co1 P2 C6 C5 52.61(17) . . . . ? C11 C10 C9 C8 -1.4(4) . . . . ? C7 C8 C9 C10 0.9(4) . . . . ? C4 C3 C2 Co1 -61.99(19) . . . . ? C1 Co1 C2 C3 133.17(16) . . . . ? C4 Co1 C2 C3 35.46(16) . . . . ? P1 Co1 C2 C3 -117.71(14) . . . . ? P2 Co1 C2 C3 -34.3(2) . . . . ? C25 C26 C27 C28 -0.2(4) . . . . ? C29 C28 C27 C26 0.5(4) . . . . ? C21 C20 C19 C24 1.5(3) . . . . ? C21 C20 C19 P2 -171.62(19) . . . . ? C23 C24 C19 C20 -3.3(3) . . . . ? C23 C24 C19 P2 169.35(18) . . . . ? C25 P2 C19 C20 -91.0(2) . . . . ? C6 P2 C19 C20 159.96(18) . . . . ? Co1 P2 C19 C20 45.0(2) . . . . ? C25 P2 C19 C24 96.3(2) . . . . ? C6 P2 C19 C24 -12.7(2) . . . . ? Co1 P2 C19 C24 -127.64(18) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.587 _refine_diff_density_min -0.607 _refine_diff_density_rms 0.064 # Attachment 'sbd0419.cif' data_sbd0419 _database_code_depnum_ccdc_archive 'CCDC 701812' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 Co O2 P' _chemical_formula_sum 'C18 H18 Co O2 P' _chemical_formula_weight 356.22 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.2928(17) _cell_length_b 13.6440(16) _cell_length_c 15.9287(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3323.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 388(2) _cell_measurement_reflns_used 6315 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 30.00 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 1.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.736 _exptl_absorpt_correction_T_max 0.893 _exptl_absorpt_process_details 'SADABS v2.03; (sheldrich)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 388(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35594 _diffrn_reflns_av_R_equivalents 0.0696 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 30.98 _reflns_number_total 5049 _reflns_number_gt 3833 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0483P)^2^+4.4418P] 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 5049 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.1133 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2132(2) 0.2149(2) 0.15259(17) 0.0288(6) Uani 1 1 d . . . C2 C 0.32648(17) 0.3871(2) 0.19646(16) 0.0249(5) Uani 1 1 d . . . C3 C 0.1754(2) 0.4167(2) 0.10200(18) 0.0324(6) Uani 1 1 d . . . H3A H 0.1623 0.3545 0.0816 0.039 Uiso 1 1 calc R . . H3B H 0.2095 0.4592 0.0703 0.039 Uiso 1 1 calc R . . C4 C 0.14322(19) 0.4465(2) 0.1814(2) 0.0335(6) Uani 1 1 d . . . H4 H 0.1553 0.5082 0.2033 0.040 Uiso 1 1 calc R . . C5 C 0.0936(2) 0.3800(3) 0.2240(2) 0.0422(8) Uani 1 1 d . . . H5A H 0.0826 0.3188 0.2006 0.051 Uiso 1 1 calc R . . H5B H 0.0709 0.3958 0.2764 0.051 Uiso 1 1 calc R . . C6 C 0.13918(15) 0.21680(17) 0.37198(15) 0.0182(4) Uani 1 1 d . . . C7 C 0.12790(16) 0.12004(18) 0.34513(16) 0.0215(5) Uani 1 1 d . . . H7 H 0.1683 0.0922 0.3085 0.026 Uiso 1 1 calc R . . C8 C 0.05741(17) 0.06535(19) 0.37239(18) 0.0269(6) Uani 1 1 d . . . H8 H 0.0507 0.0011 0.3541 0.032 Uiso 1 1 calc R . . C9 C -0.00320(18) 0.1057(2) 0.42683(19) 0.0303(6) Uani 1 1 d . . . H9 H -0.0507 0.0689 0.4450 0.036 Uiso 1 1 calc R . . C10 C 0.00727(19) 0.2012(2) 0.4540(2) 0.0373(7) Uani 1 1 d . . . H10 H -0.0334 0.2286 0.4905 0.045 Uiso 1 1 calc R . . C11 C 0.07856(18) 0.25695(19) 0.42688(19) 0.0300(6) Uani 1 1 d . . . H11 H 0.0854 0.3210 0.4457 0.036 Uiso 1 1 calc R . . C12 C 0.32290(15) 0.20475(16) 0.36078(15) 0.0172(4) Uani 1 1 d . . . C13 C 0.32339(16) 0.16214(18) 0.44006(16) 0.0215(5) Uani 1 1 d . . . H13 H 0.2781 0.1751 0.4774 0.026 Uiso 1 1 calc R . . C14 C 0.39121(17) 0.10018(19) 0.46372(17) 0.0265(5) Uani 1 1 d . . . H14 H 0.3907 0.0708 0.5164 0.032 Uiso 1 1 calc R . . C15 C 0.45930(17) 0.0823(2) 0.40894(18) 0.0275(6) Uani 1 1 d . . . H15 H 0.5049 0.0413 0.4251 0.033 Uiso 1 1 calc R . . C16 C 0.46003(18) 0.1248(2) 0.33046(18) 0.0284(6) Uani 1 1 d . . . H16 H 0.5061 0.1129 0.2938 0.034 Uiso 1 1 calc R . . C17 C 0.39121(17) 0.18589(18) 0.30628(16) 0.0232(5) Uani 1 1 d . . . H17 H 0.3913 0.2141 0.2531 0.028 Uiso 1 1 calc R . . C18 C 0.24538(19) 0.38600(18) 0.40585(17) 0.0264(5) Uani 1 1 d . . . H18A H 0.1983 0.4319 0.3991 0.040 Uiso 1 1 calc R . . H18B H 0.3000 0.4185 0.3957 0.040 Uiso 1 1 calc R . . H18C H 0.2447 0.3605 0.4620 0.040 Uiso 1 1 calc R . . Co1 Co 0.22306(2) 0.33125(2) 0.20110(2) 0.01740(10) Uani 1 1 d . . . O1 O 0.2099(2) 0.13922(16) 0.12162(15) 0.0508(7) Uani 1 1 d . . . O2 O 0.39363(14) 0.42398(18) 0.19154(14) 0.0391(5) Uani 1 1 d . . . P1 P 0.23225(4) 0.28594(4) 0.33149(4) 0.01608(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0425(16) 0.0241(12) 0.0198(13) 0.0021(10) 0.0039(11) 0.0026(11) C2 0.0217(12) 0.0331(13) 0.0199(12) 0.0040(10) 0.0003(10) 0.0000(10) C3 0.0383(16) 0.0316(14) 0.0272(14) 0.0069(11) -0.0005(12) 0.0143(12) C4 0.0308(15) 0.0306(14) 0.0390(17) 0.0028(12) -0.0006(12) 0.0113(11) C5 0.0269(15) 0.0433(17) 0.056(2) 0.0135(15) 0.0068(14) 0.0168(13) C6 0.0154(10) 0.0193(10) 0.0199(12) 0.0027(9) -0.0002(8) 0.0003(8) C7 0.0233(12) 0.0207(11) 0.0203(12) -0.0008(9) -0.0027(9) -0.0011(9) C8 0.0250(13) 0.0243(12) 0.0313(15) 0.0013(10) -0.0047(11) -0.0067(10) C9 0.0186(12) 0.0334(14) 0.0390(16) 0.0102(12) 0.0013(11) -0.0066(10) C10 0.0248(14) 0.0326(14) 0.055(2) 0.0027(13) 0.0191(14) 0.0037(11) C11 0.0260(13) 0.0209(11) 0.0431(17) 0.0004(11) 0.0137(12) 0.0022(10) C12 0.0147(10) 0.0166(10) 0.0203(12) -0.0018(8) -0.0011(9) -0.0006(8) C13 0.0179(11) 0.0266(11) 0.0201(12) 0.0000(9) 0.0000(9) 0.0002(9) C14 0.0260(13) 0.0304(13) 0.0232(13) 0.0051(10) -0.0053(10) 0.0025(10) C15 0.0235(12) 0.0292(13) 0.0298(14) -0.0015(11) -0.0058(11) 0.0105(10) C16 0.0217(12) 0.0332(14) 0.0303(14) -0.0023(11) 0.0035(11) 0.0099(10) C17 0.0246(12) 0.0250(12) 0.0199(12) 0.0022(9) 0.0009(10) 0.0061(9) C18 0.0367(14) 0.0185(11) 0.0242(13) -0.0050(10) 0.0040(11) -0.0039(10) Co1 0.01627(16) 0.01686(15) 0.01908(17) 0.00201(12) 0.00053(12) 0.00249(11) O1 0.093(2) 0.0272(11) 0.0317(12) -0.0066(9) 0.0069(13) 0.0024(12) O2 0.0278(11) 0.0534(14) 0.0360(12) 0.0069(10) 0.0004(9) -0.0113(10) P1 0.0156(3) 0.0137(2) 0.0190(3) -0.0003(2) 0.0021(2) 0.0004(2) _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 C1 O1 1.146(3) . ? C1 Co1 1.772(3) . ? C2 O2 1.146(3) . ? C2 Co1 1.757(3) . ? C3 C4 1.416(4) . ? C3 Co1 2.093(3) . ? C3 H3A 0.9300 . ? C3 H3B 0.9300 . ? C4 C5 1.364(4) . ? C4 Co1 2.016(3) . ? C4 H4 0.9300 . ? C5 Co1 2.119(3) . ? C5 H5A 0.9300 . ? C5 H5B 0.9300 . ? C6 C11 1.387(3) . ? C6 C7 1.398(3) . ? C6 P1 1.825(2) . ? C7 C8 1.381(4) . ? C7 H7 0.9300 . ? C8 C9 1.384(4) . ? C8 H8 0.9300 . ? C9 C10 1.382(4) . ? C9 H9 0.9300 . ? C10 C11 1.397(4) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C17 1.382(3) . ? C12 C13 1.390(3) . ? C12 P1 1.835(2) . ? C13 C14 1.390(3) . ? C13 H13 0.9300 . ? C14 C15 1.380(4) . ? C14 H14 0.9300 . ? C15 C16 1.378(4) . ? C15 H15 0.9300 . ? C16 C17 1.396(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 P1 1.818(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? Co1 P1 2.1715(7) . ? 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 C1 Co1 177.6(3) . . ? O2 C2 Co1 178.4(2) . . ? C4 C3 Co1 66.91(16) . . ? C4 C3 H3A 120.0 . . ? Co1 C3 H3A 80.3 . . ? C4 C3 H3B 120.0 . . ? Co1 C3 H3B 124.1 . . ? H3A C3 H3B 120.0 . . ? C5 C4 C3 116.5(3) . . ? C5 C4 Co1 74.92(18) . . ? C3 C4 Co1 72.82(16) . . ? C5 C4 H4 121.8 . . ? C3 C4 H4 121.8 . . ? Co1 C4 H4 121.8 . . ? C4 C5 Co1 66.67(17) . . ? C4 C5 H5A 120.0 . . ? Co1 C5 H5A 79.6 . . ? C4 C5 H5B 120.0 . . ? Co1 C5 H5B 125.2 . . ? H5A C5 H5B 120.0 . . ? C11 C6 C7 118.9(2) . . ? C11 C6 P1 122.66(19) . . ? C7 C6 P1 118.43(18) . . ? C8 C7 C6 120.7(2) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C7 C8 C9 120.3(3) . . ? C7 C8 H8 119.8 . . ? C9 C8 H8 119.8 . . ? C10 C9 C8 119.6(2) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C11 120.4(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C6 C11 C10 120.1(3) . . ? C6 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C17 C12 C13 119.2(2) . . ? C17 C12 P1 121.57(19) . . ? C13 C12 P1 119.18(18) . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C17 119.7(2) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C12 C17 C16 120.5(2) . . ? C12 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? P1 C18 H18A 109.5 . . ? P1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? P1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C2 Co1 C1 116.52(13) . . ? C2 Co1 C4 101.56(13) . . ? C1 Co1 C4 125.41(13) . . ? C2 Co1 C3 92.32(12) . . ? C1 Co1 C3 98.06(12) . . ? C4 Co1 C3 40.27(12) . . ? C2 Co1 C5 135.39(14) . . ? C1 Co1 C5 106.05(15) . . ? C4 Co1 C5 38.41(12) . . ? C3 Co1 C5 68.26(12) . . ? C2 Co1 P1 96.05(9) . . ? C1 Co1 P1 99.65(9) . . ? C4 Co1 P1 114.23(9) . . ? C3 Co1 P1 154.46(8) . . ? C5 Co1 P1 89.16(10) . . ? C18 P1 C6 104.12(12) . . ? C18 P1 C12 101.78(12) . . ? C6 P1 C12 100.79(10) . . ? C18 P1 Co1 114.61(9) . . ? C6 P1 Co1 115.76(8) . . ? C12 P1 Co1 117.65(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 Co1 C3 C4 C5 -62.7(2) . . . . ? C3 C4 C5 Co1 61.6(2) . . . . ? C11 C6 C7 C8 0.3(4) . . . . ? P1 C6 C7 C8 -178.5(2) . . . . ? C6 C7 C8 C9 0.0(4) . . . . ? C7 C8 C9 C10 -0.1(4) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C7 C6 C11 C10 -0.5(4) . . . . ? P1 C6 C11 C10 178.2(2) . . . . ? C9 C10 C11 C6 0.4(5) . . . . ? C17 C12 C13 C14 -0.9(4) . . . . ? P1 C12 C13 C14 179.9(2) . . . . ? C12 C13 C14 C15 1.3(4) . . . . ? C13 C14 C15 C16 -0.6(4) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C13 C12 C17 C16 0.0(4) . . . . ? P1 C12 C17 C16 179.2(2) . . . . ? C15 C16 C17 C12 0.7(4) . . . . ? C5 C4 Co1 C2 -155.7(2) . . . . ? C3 C4 Co1 C2 79.8(2) . . . . ? C5 C4 Co1 C1 69.5(3) . . . . ? C3 C4 Co1 C1 -55.0(2) . . . . ? C5 C4 Co1 C3 124.5(3) . . . . ? C3 C4 Co1 C5 -124.5(3) . . . . ? C5 C4 Co1 P1 -53.6(2) . . . . ? C3 C4 Co1 P1 -178.10(16) . . . . ? C4 C3 Co1 C2 -105.2(2) . . . . ? C4 C3 Co1 C1 137.6(2) . . . . ? C4 C3 Co1 C5 33.4(2) . . . . ? C4 C3 Co1 P1 4.0(3) . . . . ? C4 C5 Co1 C2 35.0(3) . . . . ? C4 C5 Co1 C1 -127.4(2) . . . . ? C4 C5 Co1 C3 -35.0(2) . . . . ? C4 C5 Co1 P1 132.8(2) . . . . ? C11 C6 P1 C18 20.4(3) . . . . ? C7 C6 P1 C18 -160.8(2) . . . . ? C11 C6 P1 C12 125.6(2) . . . . ? C7 C6 P1 C12 -55.6(2) . . . . ? C11 C6 P1 Co1 -106.3(2) . . . . ? C7 C6 P1 Co1 72.5(2) . . . . ? C17 C12 P1 C18 -115.4(2) . . . . ? C13 C12 P1 C18 63.8(2) . . . . ? C17 C12 P1 C6 137.5(2) . . . . ? C13 C12 P1 C6 -43.3(2) . . . . ? C17 C12 P1 Co1 10.7(2) . . . . ? C13 C12 P1 Co1 -170.12(16) . . . . ? C2 Co1 P1 C18 60.78(14) . . . . ? C1 Co1 P1 C18 179.04(14) . . . . ? C4 Co1 P1 C18 -44.81(15) . . . . ? C3 Co1 P1 C18 -47.7(2) . . . . ? C5 Co1 P1 C18 -74.81(15) . . . . ? C2 Co1 P1 C6 -177.95(12) . . . . ? C1 Co1 P1 C6 -59.69(13) . . . . ? C4 Co1 P1 C6 76.46(13) . . . . ? C3 Co1 P1 C6 73.6(2) . . . . ? C5 Co1 P1 C6 46.45(13) . . . . ? C2 Co1 P1 C12 -58.79(12) . . . . ? C1 Co1 P1 C12 59.48(13) . . . . ? C4 Co1 P1 C12 -164.38(13) . . . . ? C3 Co1 P1 C12 -167.2(2) . . . . ? C5 Co1 P1 C12 165.62(13) . . . . ? _diffrn_measured_fraction_theta_max 0.955 _diffrn_reflns_theta_full 30.98 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 1.234 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.099 # Attachment 'sbd0420m.cif' data_sbd0420m _database_code_depnum_ccdc_archive 'CCDC 701813' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H15 Co O3 P' _chemical_formula_sum 'C21 H15 Co O3 P' _chemical_formula_weight 405.23 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' Co Co 0.3494 0.9721 '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 Hexagonal _symmetry_space_group_name_H-M R-3 _symmetry_space_group_name_Hall '-R 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 15.2724(19) _cell_length_b 15.2724(19) _cell_length_c 13.854(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2798.5(9) _cell_formula_units_Z 6 _cell_measurement_temperature 393(2) _cell_measurement_reflns_used 4772 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 24.91 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1242 _exptl_absorpt_coefficient_mu 1.022 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.769 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 393(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6523 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1091 _reflns_number_gt 1013 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0419P)^2^+1.2809P] 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 1091 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0242 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0671 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.71447(11) 0.24831(11) 0.41945(10) 0.0224(3) Uani 1 1 d . . . C2 C 0.76876(11) 0.32046(11) 0.64104(10) 0.0233(4) Uani 1 1 d . . . C3 C 0.86568(13) 0.37626(14) 0.60310(12) 0.0344(4) Uani 1 1 d . . . H3 H 0.8773 0.4182 0.5502 0.041 Uiso 1 1 calc R . . C4 C 0.94508(14) 0.36951(17) 0.64384(14) 0.0450(5) Uani 1 1 d . . . H4 H 1.0099 0.4077 0.6187 0.054 Uiso 1 1 calc R . . C5 C 0.92813(16) 0.30623(17) 0.72177(14) 0.0462(5) Uani 1 1 d . . . H5 H 0.9814 0.3016 0.7487 0.055 Uiso 1 1 calc R . . C6 C 0.83251(16) 0.25032(15) 0.75913(13) 0.0418(5) Uani 1 1 d . . . H6 H 0.8211 0.2076 0.8113 0.050 Uiso 1 1 calc R . . C7 C 0.75257(14) 0.25721(13) 0.71930(12) 0.0299(4) Uani 1 1 d . . . H7 H 0.6880 0.2193 0.7452 0.036 Uiso 1 1 calc R . . Co1 Co 0.6667 0.3333 0.42899(2) 0.01699(15) Uani 1 3 d S . . O1 O 0.74541(9) 0.19376(9) 0.41499(8) 0.0324(3) Uani 1 1 d . . . P1 P 0.6667 0.3333 0.58703(4) 0.01828(18) Uani 1 3 d S . . 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 C1 0.0240(8) 0.0235(8) 0.0167(7) -0.0006(6) -0.0027(6) 0.0096(7) C2 0.0263(8) 0.0281(8) 0.0184(8) -0.0070(6) -0.0054(6) 0.0157(7) C3 0.0279(9) 0.0457(10) 0.0264(9) -0.0032(7) -0.0050(7) 0.0159(8) C4 0.0271(9) 0.0664(13) 0.0410(11) -0.0148(10) -0.0084(8) 0.0229(9) C5 0.0478(12) 0.0707(14) 0.0396(11) -0.0200(10) -0.0209(9) 0.0441(11) C6 0.0578(12) 0.0548(12) 0.0312(10) -0.0047(8) -0.0119(9) 0.0419(11) C7 0.0386(9) 0.0374(9) 0.0220(8) -0.0012(7) -0.0035(7) 0.0252(8) Co1 0.01867(17) 0.01867(17) 0.0136(2) 0.000 0.000 0.00933(9) O1 0.0400(7) 0.0329(6) 0.0339(7) -0.0025(5) -0.0051(5) 0.0254(6) P1 0.0204(2) 0.0204(2) 0.0141(3) 0.000 0.000 0.01018(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 C1 O1 1.1467(19) . ? C1 Co1 1.7845(16) . ? C2 C7 1.390(2) . ? C2 C3 1.390(2) . ? C2 P1 1.8265(15) . ? C3 C4 1.387(3) . ? C3 H3 0.9300 . ? C4 C5 1.384(3) . ? C4 H4 0.9300 . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C6 C7 1.391(2) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? Co1 C1 1.7845(16) 2_655 ? Co1 C1 1.7845(16) 3_665 ? Co1 P1 2.1895(9) . ? Co1 Co1 2.6506(9) 16_655 ? P1 C2 1.8265(15) 3_665 ? P1 C2 1.8265(15) 2_655 ? 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 C1 Co1 178.83(13) . . ? C7 C2 C3 119.08(15) . . ? C7 C2 P1 121.99(12) . . ? C3 C2 P1 118.93(12) . . ? C4 C3 C2 120.19(17) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.26(18) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C6 C5 C4 119.86(17) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C5 C6 C7 120.31(18) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C2 C7 C6 120.29(17) . . ? C2 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C1 Co1 C1 119.457(12) . 2_655 ? C1 Co1 C1 119.457(12) . 3_665 ? C1 Co1 C1 119.457(12) 2_655 3_665 ? C1 Co1 P1 94.25(5) . . ? C1 Co1 P1 94.25(5) 2_655 . ? C1 Co1 P1 94.25(5) 3_665 . ? C1 Co1 Co1 85.75(5) . 16_655 ? C1 Co1 Co1 85.75(5) 2_655 16_655 ? C1 Co1 Co1 85.75(5) 3_665 16_655 ? P1 Co1 Co1 180.0 . 16_655 ? C2 P1 C2 104.37(6) . 3_665 ? C2 P1 C2 104.37(6) . 2_655 ? C2 P1 C2 104.37(6) 3_665 2_655 ? C2 P1 Co1 114.18(5) . . ? C2 P1 Co1 114.18(5) 3_665 . ? C2 P1 Co1 114.18(5) 2_655 . ? 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 C7 C2 C3 C4 -0.8(2) . . . . ? P1 C2 C3 C4 178.74(14) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 C7 -0.2(3) . . . . ? C3 C2 C7 C6 0.2(2) . . . . ? P1 C2 C7 C6 -179.27(13) . . . . ? C5 C6 C7 C2 0.3(3) . . . . ? C7 C2 P1 C2 -11.36(15) . . . 3_665 ? C3 C2 P1 C2 169.15(12) . . . 3_665 ? C7 C2 P1 C2 97.92(10) . . . 2_655 ? C3 C2 P1 C2 -81.57(17) . . . 2_655 ? C7 C2 P1 Co1 -136.72(12) . . . . ? C3 C2 P1 Co1 43.79(14) . . . . ? C1 Co1 P1 C2 33.32(7) . . . . ? C1 Co1 P1 C2 -86.68(7) 2_655 . . . ? C1 Co1 P1 C2 153.32(7) 3_665 . . . ? C1 Co1 P1 C2 -86.68(7) . . . 3_665 ? C1 Co1 P1 C2 153.32(7) 2_655 . . 3_665 ? C1 Co1 P1 C2 33.32(7) 3_665 . . 3_665 ? C1 Co1 P1 C2 153.32(7) . . . 2_655 ? C1 Co1 P1 C2 33.32(7) 2_655 . . 2_655 ? C1 Co1 P1 C2 -86.68(7) 3_665 . . 2_655 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.339 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.052