# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_publication_text _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Robert Beck' _publ_contact_author_address ;Technische Universit\"at Darmstadt Eduard Zintl Institut Petersenstrasse 18 64287 Darmstadt Germany ; _publ_contact_author_email metallacycle@gmail loop_ _publ_author_name _publ_author_address S.Camadanli ;Technische Universit\"at Darmstadt Eduard Zintl Institut Petersenstrasse 18 64287 Darmstadt Germany ; R.Beck ;Technische Universit\"at Darmstadt Eduard Zintl Institut Petersenstrasse 18 64287 Darmstadt Germany ; H.-F.Klein ;Technische Universit\"at Darmstadt Eduard Zintl Institut Petersenstrasse 18 64287 Darmstadt Germany ; # Attachment '3.cif' data_c:\structures\ _database_code_depnum_ccdc_archive 'CCDC 674147' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 Co F4 O P3' _chemical_formula_weight 540.32 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' F F 0.0171 0.0103 '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 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 12.7954(16) _cell_length_b 14.830(2) _cell_length_c 17.434(2) _cell_angle_alpha 90.00 _cell_angle_beta 130.890(8) _cell_angle_gamma 90.00 _cell_volume 2500.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 0.920 _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 150(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 'Stoe IPDS II' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 34404 _diffrn_reflns_av_R_equivalents 0.1791 _diffrn_reflns_av_sigmaI/netI 0.0945 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 26.88 _reflns_number_total 5329 _reflns_number_gt 3845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XAREA (STOE, 2002)' _computing_cell_refinement 'XAREA (STOE, 2002)' _computing_data_reduction 'X-Red (STOE, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material 'X-STEP32, Microsoft Word' _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^)+(0.0357P)^2^+0.4188P] 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 5329 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0916 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1067 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C1 C 0.4033(4) 0.0681(2) -0.2807(3) 0.0230(8) Uani 1 1 d . . . C2 C 0.3606(4) 0.0193(2) -0.2372(3) 0.0244(8) Uani 1 1 d . . . C3 C 0.2259(4) 0.0142(2) -0.2768(3) 0.0263(9) Uani 1 1 d . . . C4 C 0.1229(4) 0.0580(3) -0.3672(3) 0.0266(8) Uani 1 1 d . . . C5 C 0.1559(4) 0.1048(3) -0.4153(3) 0.0257(8) Uani 1 1 d . . . C6 C 0.2929(4) 0.1090(2) -0.3774(3) 0.0218(8) Uani 1 1 d . . . C7 C 0.3413(4) 0.1545(2) -0.4211(3) 0.0196(7) Uani 1 1 d . . . C8 C 0.2596(3) 0.1919(2) -0.5239(3) 0.0197(7) Uani 1 1 d . . . C9 C 0.1417(4) 0.1486(3) -0.6093(3) 0.0257(8) Uani 1 1 d . . . H9A H 0.1115 0.0950 -0.6016 0.031 Uiso 1 1 calc R . . C10 C 0.0700(4) 0.1853(3) -0.7051(3) 0.0306(9) Uani 1 1 d . . . H10A H -0.0078 0.1558 -0.7614 0.037 Uiso 1 1 calc R . . C11 C 0.1126(4) 0.2650(3) -0.7181(3) 0.0320(9) Uani 1 1 d . . . H11A H 0.0627 0.2897 -0.7825 0.038 Uiso 1 1 calc R . . C12 C 0.2294(4) 0.3078(3) -0.6350(3) 0.0304(9) Uani 1 1 d . . . H12A H 0.2585 0.3614 -0.6434 0.036 Uiso 1 1 calc R . . C13 C 0.3034(4) 0.2713(3) -0.5391(3) 0.0253(8) Uani 1 1 d . . . H13A H 0.3836 0.2998 -0.4839 0.030 Uiso 1 1 calc R . . C14 C 0.5697(5) 0.1552(3) -0.0478(4) 0.0365(10) Uani 1 1 d . . . H14A H 0.6276 0.1747 0.0216 0.055 Uiso 1 1 calc R . . H14B H 0.5186 0.1028 -0.0569 0.055 Uiso 1 1 calc R . . H14C H 0.5065 0.2026 -0.0914 0.055 Uiso 1 1 calc R . . C15 C 0.7879(5) 0.0405(3) 0.0146(3) 0.0398(11) Uani 1 1 d . . . H15A H 0.7362 -0.0144 -0.0048 0.060 Uiso 1 1 calc R . . H15B H 0.8206 0.0596 0.0797 0.060 Uiso 1 1 calc R . . H15C H 0.8654 0.0303 0.0185 0.060 Uiso 1 1 calc R . . C16 C 0.7919(5) 0.2254(3) -0.0162(3) 0.0406(11) Uani 1 1 d . . . H16A H 0.8256 0.2299 0.0516 0.061 Uiso 1 1 calc R . . H16B H 0.7417 0.2792 -0.0532 0.061 Uiso 1 1 calc R . . H16C H 0.8684 0.2184 -0.0140 0.061 Uiso 1 1 calc R . . C17 C 0.5551(6) -0.1388(3) -0.2250(4) 0.0405(11) Uani 1 1 d . . . H17A H 0.6052 -0.1404 -0.1534 0.061 Uiso 1 1 calc R . . H17B H 0.5694 -0.1942 -0.2454 0.061 Uiso 1 1 calc R . . H17C H 0.4583 -0.1313 -0.2612 0.061 Uiso 1 1 calc R . . C18 C 0.7890(5) -0.0880(3) -0.1907(4) 0.0473(12) Uani 1 1 d . . . H18A H 0.7828 -0.1499 -0.2094 0.071 Uiso 1 1 calc R . . H18B H 0.8447 -0.0838 -0.1185 0.071 Uiso 1 1 calc R . . H18C H 0.8305 -0.0531 -0.2110 0.071 Uiso 1 1 calc R . . C19 C 0.5264(6) -0.0695(3) -0.3864(4) 0.0487(13) Uani 1 1 d . . . H19A H 0.4298 -0.0563 -0.4271 0.073 Uiso 1 1 calc R . . H19B H 0.5379 -0.1321 -0.3934 0.073 Uiso 1 1 calc R . . H19C H 0.5643 -0.0331 -0.4086 0.073 Uiso 1 1 calc R . . C20 C 0.9373(4) 0.1311(3) -0.1192(3) 0.0342(10) Uani 1 1 d . . . H20A H 0.9918 0.1618 -0.1310 0.051 Uiso 1 1 calc R . . H20B H 0.9555 0.0676 -0.1130 0.051 Uiso 1 1 calc R . . H20C H 0.9610 0.1533 -0.0578 0.051 Uiso 1 1 calc R . . C21 C 0.7413(5) 0.1229(3) -0.3332(3) 0.0372(10) Uani 1 1 d . . . H21A H 0.7589 0.0597 -0.3315 0.056 Uiso 1 1 calc R . . H21B H 0.8081 0.1571 -0.3297 0.056 Uiso 1 1 calc R . . H21C H 0.6501 0.1369 -0.3952 0.056 Uiso 1 1 calc R . . C22 C 0.7503(4) 0.2738(3) -0.2354(3) 0.0311(9) Uani 1 1 d . . . H22A H 0.7687 0.3001 -0.1773 0.047 Uiso 1 1 calc R . . H22B H 0.6607 0.2926 -0.2959 0.047 Uiso 1 1 calc R . . H22C H 0.8193 0.2931 -0.2382 0.047 Uiso 1 1 calc R . . Co1 Co 0.58292(5) 0.09637(3) -0.23658(4) 0.01761(13) Uani 1 1 d . . . F1 F 0.4556(3) -0.02517(15) -0.14669(17) 0.0318(5) Uani 1 1 d . . . F2 F 0.1928(3) -0.03117(15) -0.2274(2) 0.0376(6) Uani 1 1 d . . . F3 F -0.0087(2) 0.05635(17) -0.4025(2) 0.0402(6) Uani 1 1 d . . . F4 F 0.0514(2) 0.15077(17) -0.50058(19) 0.0377(6) Uani 1 1 d . . . O1 O 0.4744(2) 0.16169(16) -0.36119(18) 0.0194(5) Uani 1 1 d . . . P1 P 0.67717(10) 0.12768(7) -0.07942(8) 0.0228(2) Uani 1 1 d . . . P2 P 0.75430(10) 0.15164(6) -0.22545(8) 0.0215(2) Uani 1 1 d . . . P3 P 0.61630(11) -0.04486(6) -0.25359(8) 0.0243(2) 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 0.028(2) 0.0190(17) 0.025(2) -0.0026(14) 0.0182(18) -0.0062(15) C2 0.034(2) 0.0168(17) 0.026(2) -0.0006(15) 0.0208(19) -0.0025(16) C3 0.042(2) 0.0182(18) 0.039(2) -0.0073(16) 0.036(2) -0.0100(17) C4 0.024(2) 0.0243(19) 0.036(2) -0.0079(17) 0.0223(19) -0.0071(16) C5 0.0217(18) 0.028(2) 0.027(2) -0.0017(17) 0.0160(17) -0.0028(16) C6 0.0217(18) 0.0183(18) 0.0246(19) -0.0025(15) 0.0149(17) -0.0020(14) C7 0.0185(18) 0.0172(17) 0.0210(19) -0.0019(14) 0.0119(16) -0.0002(14) C8 0.0150(17) 0.0198(17) 0.0233(19) 0.0024(14) 0.0122(16) 0.0027(14) C9 0.0240(19) 0.028(2) 0.023(2) -0.0018(16) 0.0142(17) -0.0012(16) C10 0.0222(19) 0.043(2) 0.022(2) -0.0037(18) 0.0128(18) -0.0022(18) C11 0.024(2) 0.047(3) 0.022(2) 0.0104(18) 0.0140(19) 0.0095(18) C12 0.031(2) 0.030(2) 0.031(2) 0.0082(17) 0.021(2) 0.0018(17) C13 0.0231(19) 0.027(2) 0.025(2) 0.0034(16) 0.0154(18) 0.0004(16) C14 0.038(2) 0.039(2) 0.042(3) -0.013(2) 0.030(2) -0.004(2) C15 0.044(3) 0.041(3) 0.025(2) 0.0050(19) 0.019(2) 0.012(2) C16 0.037(2) 0.050(3) 0.030(2) -0.014(2) 0.020(2) -0.014(2) C17 0.066(3) 0.023(2) 0.053(3) -0.001(2) 0.048(3) -0.003(2) C18 0.058(3) 0.027(2) 0.069(4) 0.004(2) 0.047(3) 0.013(2) C19 0.078(4) 0.034(2) 0.038(3) -0.011(2) 0.040(3) -0.015(2) C20 0.027(2) 0.032(2) 0.039(3) 0.0055(19) 0.020(2) 0.0061(17) C21 0.045(3) 0.043(3) 0.033(2) 0.0027(19) 0.029(2) -0.003(2) C22 0.025(2) 0.026(2) 0.038(2) 0.0050(18) 0.019(2) 0.0007(17) Co1 0.0181(2) 0.0155(2) 0.0175(2) 0.0021(2) 0.0109(2) 0.0005(2) F1 0.0446(14) 0.0267(12) 0.0302(13) 0.0067(10) 0.0271(12) 0.0000(10) F2 0.0599(17) 0.0285(12) 0.0553(17) -0.0041(11) 0.0511(15) -0.0110(12) F3 0.0324(13) 0.0443(14) 0.0595(17) -0.0099(13) 0.0369(14) -0.0110(11) F4 0.0223(12) 0.0464(15) 0.0382(15) 0.0107(12) 0.0171(12) 0.0057(11) O1 0.0165(12) 0.0185(12) 0.0188(13) 0.0031(10) 0.0096(11) 0.0006(10) P1 0.0235(5) 0.0228(5) 0.0205(5) -0.0006(4) 0.0138(4) 0.0027(4) P2 0.0182(5) 0.0208(5) 0.0236(5) 0.0038(4) 0.0129(4) 0.0019(4) P3 0.0355(6) 0.0176(5) 0.0247(5) -0.0003(4) 0.0219(5) 0.0001(4) _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 C2 1.393(5) . ? C1 C6 1.444(5) . ? C1 Co1 1.932(4) . ? C2 F1 1.376(4) . ? C2 C3 1.378(6) . ? C3 F2 1.361(4) . ? C3 C4 1.387(6) . ? C4 C5 1.352(5) . ? C4 F3 1.363(4) . ? C5 F4 1.364(4) . ? C5 C6 1.413(5) . ? C6 C7 1.428(5) . ? C7 O1 1.293(4) . ? C7 C8 1.470(5) . ? C8 C9 1.401(5) . ? C8 C13 1.402(5) . ? C9 C10 1.386(6) . ? C10 C11 1.381(6) . ? C11 C12 1.378(6) . ? C12 C13 1.383(5) . ? C14 P1 1.832(4) . ? C15 P1 1.824(4) . ? C16 P1 1.830(4) . ? C17 P3 1.820(4) . ? C18 P3 1.823(5) . ? C19 P3 1.825(5) . ? C20 P2 1.824(4) . ? C21 P2 1.825(4) . ? C22 P2 1.817(4) . ? Co1 O1 1.907(2) . ? Co1 P3 2.1962(11) . ? Co1 P1 2.2026(11) . ? Co1 P2 2.2273(11) . ? 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 C2 C1 C6 114.9(3) . . ? C2 C1 Co1 133.1(3) . . ? C6 C1 Co1 112.0(2) . . ? F1 C2 C3 115.0(3) . . ? F1 C2 C1 120.5(3) . . ? C3 C2 C1 124.4(4) . . ? F2 C3 C2 121.1(4) . . ? F2 C3 C4 119.6(3) . . ? C2 C3 C4 119.3(3) . . ? C5 C4 F3 121.6(4) . . ? C5 C4 C3 119.7(3) . . ? F3 C4 C3 118.6(3) . . ? C4 C5 F4 116.8(3) . . ? C4 C5 C6 121.9(4) . . ? F4 C5 C6 121.2(3) . . ? C5 C6 C7 127.6(3) . . ? C5 C6 C1 119.6(3) . . ? C7 C6 C1 112.7(3) . . ? O1 C7 C6 114.2(3) . . ? O1 C7 C8 117.6(3) . . ? C6 C7 C8 128.2(3) . . ? C9 C8 C13 118.0(3) . . ? C9 C8 C7 122.3(3) . . ? C13 C8 C7 119.6(3) . . ? C10 C9 C8 120.2(4) . . ? C11 C10 C9 120.8(4) . . ? C12 C11 C10 119.7(4) . . ? C11 C12 C13 120.2(4) . . ? C12 C13 C8 121.0(4) . . ? O1 Co1 C1 82.35(13) . . ? O1 Co1 P3 113.06(8) . . ? C1 Co1 P3 91.45(11) . . ? O1 Co1 P1 135.02(8) . . ? C1 Co1 P1 94.65(11) . . ? P3 Co1 P1 111.87(4) . . ? O1 Co1 P2 81.58(8) . . ? C1 Co1 P2 163.92(12) . . ? P3 Co1 P2 95.47(4) . . ? P1 Co1 P2 96.20(4) . . ? C7 O1 Co1 118.1(2) . . ? C15 P1 C16 100.1(2) . . ? C15 P1 C14 100.5(2) . . ? C16 P1 C14 96.1(2) . . ? C15 P1 Co1 116.04(15) . . ? C16 P1 Co1 119.09(15) . . ? C14 P1 Co1 120.93(15) . . ? C22 P2 C20 101.6(2) . . ? C22 P2 C21 99.0(2) . . ? C20 P2 C21 101.4(2) . . ? C22 P2 Co1 113.18(13) . . ? C20 P2 Co1 124.30(15) . . ? C21 P2 Co1 113.79(15) . . ? C17 P3 C18 97.8(2) . . ? C17 P3 C19 99.6(2) . . ? C18 P3 C19 101.7(2) . . ? C17 P3 Co1 122.43(15) . . ? C18 P3 Co1 121.33(16) . . ? C19 P3 Co1 110.22(17) . . ? 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 C1 C2 F1 177.9(3) . . . . ? Co1 C1 C2 F1 -4.2(6) . . . . ? C6 C1 C2 C3 -4.7(5) . . . . ? Co1 C1 C2 C3 173.1(3) . . . . ? F1 C2 C3 F2 0.8(5) . . . . ? C1 C2 C3 F2 -176.7(3) . . . . ? F1 C2 C3 C4 179.2(3) . . . . ? C1 C2 C3 C4 1.7(6) . . . . ? F2 C3 C4 C5 178.5(3) . . . . ? C2 C3 C4 C5 0.1(6) . . . . ? F2 C3 C4 F3 1.9(5) . . . . ? C2 C3 C4 F3 -176.5(3) . . . . ? F3 C4 C5 F4 0.4(6) . . . . ? C3 C4 C5 F4 -176.1(3) . . . . ? F3 C4 C5 C6 178.0(3) . . . . ? C3 C4 C5 C6 1.5(6) . . . . ? C4 C5 C6 C7 179.0(4) . . . . ? F4 C5 C6 C7 -3.4(6) . . . . ? C4 C5 C6 C1 -4.8(6) . . . . ? F4 C5 C6 C1 172.7(3) . . . . ? C2 C1 C6 C5 6.1(5) . . . . ? Co1 C1 C6 C5 -172.2(3) . . . . ? C2 C1 C6 C7 -177.2(3) . . . . ? Co1 C1 C6 C7 4.5(4) . . . . ? C5 C6 C7 O1 167.5(4) . . . . ? C1 C6 C7 O1 -8.9(4) . . . . ? C5 C6 C7 C8 -13.5(6) . . . . ? C1 C6 C7 C8 170.1(3) . . . . ? O1 C7 C8 C9 140.8(3) . . . . ? C6 C7 C8 C9 -38.2(5) . . . . ? O1 C7 C8 C13 -36.0(5) . . . . ? C6 C7 C8 C13 145.0(4) . . . . ? C13 C8 C9 C10 -1.5(5) . . . . ? C7 C8 C9 C10 -178.3(3) . . . . ? C8 C9 C10 C11 -0.4(6) . . . . ? C9 C10 C11 C12 1.3(6) . . . . ? C10 C11 C12 C13 -0.1(6) . . . . ? C11 C12 C13 C8 -1.8(6) . . . . ? C9 C8 C13 C12 2.6(5) . . . . ? C7 C8 C13 C12 179.5(3) . . . . ? C2 C1 Co1 O1 -177.7(4) . . . . ? C6 C1 Co1 O1 0.2(2) . . . . ? C2 C1 Co1 P3 69.2(4) . . . . ? C6 C1 Co1 P3 -112.9(2) . . . . ? C2 C1 Co1 P1 -42.9(4) . . . . ? C6 C1 Co1 P1 135.0(2) . . . . ? C2 C1 Co1 P2 -175.2(2) . . . . ? C6 C1 Co1 P2 2.7(6) . . . . ? C6 C7 O1 Co1 9.5(4) . . . . ? C8 C7 O1 Co1 -169.6(2) . . . . ? C1 Co1 O1 C7 -5.5(3) . . . . ? P3 Co1 O1 C7 82.8(2) . . . . ? P1 Co1 O1 C7 -94.5(3) . . . . ? P2 Co1 O1 C7 175.2(2) . . . . ? O1 Co1 P1 C15 -173.9(2) . . . . ? C1 Co1 P1 C15 102.3(2) . . . . ? P3 Co1 P1 C15 8.85(19) . . . . ? P2 Co1 P1 C15 -89.60(19) . . . . ? O1 Co1 P1 C16 -54.2(2) . . . . ? C1 Co1 P1 C16 -138.0(2) . . . . ? P3 Co1 P1 C16 128.52(19) . . . . ? P2 Co1 P1 C16 30.07(19) . . . . ? O1 Co1 P1 C14 64.2(2) . . . . ? C1 Co1 P1 C14 -19.7(2) . . . . ? P3 Co1 P1 C14 -113.11(18) . . . . ? P2 Co1 P1 C14 148.44(18) . . . . ? O1 Co1 P2 C22 55.78(18) . . . . ? C1 Co1 P2 C22 53.3(4) . . . . ? P3 Co1 P2 C22 168.33(16) . . . . ? P1 Co1 P2 C22 -78.91(16) . . . . ? O1 Co1 P2 C20 179.5(2) . . . . ? C1 Co1 P2 C20 177.0(4) . . . . ? P3 Co1 P2 C20 -67.90(19) . . . . ? P1 Co1 P2 C20 44.86(18) . . . . ? O1 Co1 P2 C21 -56.25(18) . . . . ? C1 Co1 P2 C21 -58.8(4) . . . . ? P3 Co1 P2 C21 56.30(17) . . . . ? P1 Co1 P2 C21 169.06(17) . . . . ? O1 Co1 P3 C17 -118.2(2) . . . . ? C1 Co1 P3 C17 -35.9(2) . . . . ? P1 Co1 P3 C17 59.7(2) . . . . ? P2 Co1 P3 C17 158.6(2) . . . . ? O1 Co1 P3 C18 116.6(2) . . . . ? C1 Co1 P3 C18 -161.1(2) . . . . ? P1 Co1 P3 C18 -65.5(2) . . . . ? P2 Co1 P3 C18 33.5(2) . . . . ? O1 Co1 P3 C19 -1.8(2) . . . . ? C1 Co1 P3 C19 80.5(2) . . . . ? P1 Co1 P3 C19 176.10(19) . . . . ? P2 Co1 P3 C19 -84.97(19) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 26.88 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.525 _refine_diff_density_min -0.623 _refine_diff_density_rms 0.087 # Attachment '4.cif' data_c:\structures\4 _database_code_depnum_ccdc_archive 'CCDC 674148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H36 Co F O P3' _chemical_formula_weight 487.35 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' F F 0.0171 0.0103 '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/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7220(12) _cell_length_b 17.1350(13) _cell_length_c 15.4390(11) _cell_angle_alpha 90.000(12) _cell_angle_beta 101.030(12) _cell_angle_gamma 90.000(12) _cell_volume 2524.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description bloc _exptl_crystal_colour brown _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 0.887 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9010 _exptl_absorpt_correction_T_max 0.9324 _exptl_absorpt_process_details '(MULABS; Spek, 2003; Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Stoe IPDS II' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 30970 _diffrn_reflns_av_R_equivalents 0.1130 _diffrn_reflns_av_sigmaI/netI 0.0516 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 4.16 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5112 _reflns_number_gt 4494 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe X-Area' _computing_cell_refinement 'Stoe X-Area' _computing_data_reduction 'Stoe X-RED' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Diamond 2.1e' _computing_publication_material 'X-STEP32, Microsoft Word' _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^)+(0.0684P)^2^+1.0226P] 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 5112 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0522 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1153 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C1 C 0.6744(2) 0.25560(12) 0.43596(15) 0.0202(5) Uani 1 1 d . . . C2 C 0.7325(2) 0.33230(13) 0.41066(15) 0.0219(5) Uani 1 1 d . . . C3 C 0.7365(3) 0.35772(14) 0.32521(16) 0.0263(5) Uani 1 1 d . . . C4 C 0.7842(3) 0.43049(15) 0.3060(2) 0.0369(6) Uani 1 1 d . . . H5A H 0.7840 0.4449 0.2479 0.044 Uiso 1 1 calc R . . C5 C 0.8322(3) 0.48182(15) 0.3749(2) 0.0433(8) Uani 1 1 d . . . H11A H 0.8655 0.5309 0.3632 0.052 Uiso 1 1 calc R . . C6 C 0.8305(3) 0.45954(16) 0.4612(2) 0.0400(7) Uani 1 1 d . . . H7A H 0.8620 0.4938 0.5075 0.048 Uiso 1 1 calc R . . C7 C 0.7816(3) 0.38605(15) 0.47835(18) 0.0299(5) Uani 1 1 d . . . H6A H 0.7813 0.3719 0.5365 0.036 Uiso 1 1 calc R . . C8 C 0.7479(2) 0.18072(13) 0.42123(15) 0.0219(5) Uani 1 1 d . . . C9 C 0.8181(2) 0.16742(14) 0.35140(17) 0.0258(5) Uani 1 1 d . . . H2A H 0.8251 0.2076 0.3119 0.031 Uiso 1 1 calc R . . C10 C 0.8777(3) 0.09502(15) 0.34002(18) 0.0318(6) Uani 1 1 d . . . H4A H 0.9199 0.0868 0.2916 0.038 Uiso 1 1 calc R . . C11 C 0.8749(3) 0.03517(15) 0.3998(2) 0.0377(6) Uani 1 1 d . . . H9A H 0.9152 -0.0129 0.3922 0.045 Uiso 1 1 calc R . . C12 C 0.8106(3) 0.04846(16) 0.4714(2) 0.0399(7) Uani 1 1 d . . . H12A H 0.8103 0.0092 0.5130 0.048 Uiso 1 1 calc R . . C13 C 0.7466(3) 0.11936(15) 0.48196(18) 0.0311(6) Uani 1 1 d . . . H10A H 0.7024 0.1265 0.5297 0.037 Uiso 1 1 calc R . . C14 C 0.4211(3) 0.44723(15) 0.3960(2) 0.0402(7) Uani 1 1 d . . . H15A H 0.5194 0.4521 0.3956 0.048 Uiso 1 1 calc R . . H15B H 0.4061 0.4509 0.4555 0.048 Uiso 1 1 calc R . . H15C H 0.3709 0.4883 0.3612 0.048 Uiso 1 1 calc R . . C15 C 0.3604(3) 0.37029(19) 0.23147(19) 0.0440(7) Uani 1 1 d . . . H18C H 0.3102 0.4175 0.2128 0.053 Uiso 1 1 calc R . . H18B H 0.3166 0.3273 0.1969 0.053 Uiso 1 1 calc R . . H18A H 0.4556 0.3753 0.2236 0.053 Uiso 1 1 calc R . . C16 C 0.1692(3) 0.36438(17) 0.3458(2) 0.0385(6) Uani 1 1 d . . . H13A H 0.1521 0.3684 0.4049 0.046 Uiso 1 1 calc R . . H13B H 0.1199 0.3200 0.3172 0.046 Uiso 1 1 calc R . . H13C H 0.1368 0.4109 0.3136 0.046 Uiso 1 1 calc R . . C17 C 0.3356(3) 0.31548(17) 0.59481(19) 0.0398(7) Uani 1 1 d . . . H21A H 0.3002 0.3601 0.5599 0.048 Uiso 1 1 calc R . . H21B H 0.4300 0.3255 0.6246 0.048 Uiso 1 1 calc R . . H21C H 0.2779 0.3055 0.6376 0.048 Uiso 1 1 calc R . . C18 C 0.4153(3) 0.15790(17) 0.60325(19) 0.0398(7) Uani 1 1 d . . . H14A H 0.5066 0.1758 0.6311 0.048 Uiso 1 1 calc R . . H14B H 0.4238 0.1093 0.5738 0.048 Uiso 1 1 calc R . . H14C H 0.3586 0.1505 0.6471 0.048 Uiso 1 1 calc R . . C19 C 0.1494(3) 0.20093(19) 0.5079(2) 0.0415(7) Uani 1 1 d . . . H22C H 0.1219 0.1982 0.5644 0.050 Uiso 1 1 calc R . . H22B H 0.1376 0.1507 0.4800 0.050 Uiso 1 1 calc R . . H22A H 0.0921 0.2385 0.4715 0.050 Uiso 1 1 calc R . . C20 C 0.4727(3) 0.1550(2) 0.2213(2) 0.0460(8) Uani 1 1 d . . . H16A H 0.5718 0.1466 0.2387 0.055 Uiso 1 1 calc R . . H16B H 0.4562 0.2035 0.1898 0.055 Uiso 1 1 calc R . . H16C H 0.4318 0.1130 0.1839 0.055 Uiso 1 1 calc R . . C21 C 0.4200(5) 0.05707(17) 0.3567(3) 0.0606(10) Uani 1 1 d . . . H19A H 0.3696 0.0476 0.4034 0.073 Uiso 1 1 calc R . . H19B H 0.5181 0.0479 0.3779 0.073 Uiso 1 1 calc R . . H19C H 0.3863 0.0226 0.3083 0.073 Uiso 1 1 calc R . . C22 C 0.2077(3) 0.1565(2) 0.2656(2) 0.0530(9) Uani 1 1 d . . . H17C H 0.1927 0.1150 0.2232 0.064 Uiso 1 1 calc R . . H17B H 0.1827 0.2054 0.2363 0.064 Uiso 1 1 calc R . . H17A H 0.1508 0.1481 0.3092 0.064 Uiso 1 1 calc R . . Co1 Co 0.46365(3) 0.247968(15) 0.421370(19) 0.01735(11) Uani 1 1 d . . . F1 F 0.68442(17) 0.30984(9) 0.25483(9) 0.0354(4) Uani 1 1 d . . . O1 O 0.62480(18) 0.25929(9) 0.51126(11) 0.0225(3) Uani 1 1 d . . . P1 P 0.39335(7) 0.15879(4) 0.31962(4) 0.02638(16) Uani 1 1 d . . . P2 P 0.33318(7) 0.23020(4) 0.52297(4) 0.02321(15) Uani 1 1 d . . . P3 P 0.35815(7) 0.35246(4) 0.34931(4) 0.02582(16) 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 0.0187(12) 0.0230(11) 0.0180(11) 0.0000(8) 0.0012(9) -0.0018(8) C2 0.0191(11) 0.0226(10) 0.0247(12) 0.0010(9) 0.0059(9) -0.0010(8) C3 0.0258(13) 0.0259(11) 0.0294(13) -0.0007(9) 0.0108(10) 0.0029(9) C4 0.0425(16) 0.0283(12) 0.0476(16) 0.0104(12) 0.0284(13) 0.0065(11) C5 0.0418(17) 0.0210(12) 0.075(2) 0.0027(13) 0.0315(16) -0.0048(11) C6 0.0320(15) 0.0310(13) 0.0597(19) -0.0150(13) 0.0157(13) -0.0098(11) C7 0.0253(13) 0.0323(12) 0.0319(14) -0.0057(10) 0.0051(10) -0.0066(10) C8 0.0163(11) 0.0234(10) 0.0235(11) 0.0009(9) -0.0023(9) -0.0013(8) C9 0.0198(12) 0.0260(11) 0.0307(13) -0.0010(9) 0.0028(10) 0.0004(9) C10 0.0231(13) 0.0316(12) 0.0402(15) -0.0079(11) 0.0043(11) 0.0033(10) C11 0.0284(14) 0.0259(12) 0.0545(18) -0.0055(12) -0.0028(13) 0.0068(10) C12 0.0362(16) 0.0290(13) 0.0523(18) 0.0117(12) 0.0029(13) 0.0055(11) C13 0.0292(14) 0.0318(13) 0.0320(14) 0.0078(10) 0.0049(11) 0.0019(10) C14 0.0401(16) 0.0241(12) 0.0562(18) 0.0009(12) 0.0092(14) 0.0047(11) C15 0.0443(18) 0.0561(18) 0.0315(15) 0.0159(13) 0.0070(13) 0.0209(14) C16 0.0322(15) 0.0422(15) 0.0396(15) -0.0006(12) 0.0029(12) 0.0121(12) C17 0.0482(18) 0.0434(15) 0.0306(14) -0.0081(12) 0.0142(13) -0.0028(13) C18 0.0422(17) 0.0437(15) 0.0371(15) 0.0153(12) 0.0168(13) 0.0035(12) C19 0.0274(15) 0.0571(18) 0.0414(16) -0.0017(14) 0.0105(12) -0.0089(13) C20 0.0365(16) 0.066(2) 0.0351(15) -0.0273(14) 0.0065(13) -0.0002(14) C21 0.087(3) 0.0260(14) 0.062(2) -0.0102(14) -0.005(2) -0.0121(15) C22 0.0243(15) 0.069(2) 0.062(2) -0.0350(18) -0.0012(14) -0.0061(14) Co1 0.01776(19) 0.01774(17) 0.01618(18) -0.00134(10) 0.00228(13) -0.00086(10) F1 0.0445(9) 0.0367(8) 0.0260(8) 0.0034(6) 0.0090(7) 0.0047(7) O1 0.0207(8) 0.0308(8) 0.0150(8) -0.0012(6) 0.0009(6) -0.0046(6) P1 0.0220(3) 0.0283(3) 0.0275(3) -0.0111(2) 0.0014(3) -0.0027(2) P2 0.0227(3) 0.0261(3) 0.0218(3) -0.0008(2) 0.0066(2) -0.0023(2) P3 0.0264(3) 0.0260(3) 0.0244(3) 0.0035(2) 0.0033(3) 0.0071(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 1.343(3) . ? C1 C8 1.507(3) . ? C1 C2 1.511(3) . ? C1 Co1 2.022(2) . ? C2 C3 1.397(3) . ? C2 C7 1.406(3) . ? C3 F1 1.378(3) . ? C3 C4 1.382(3) . ? C4 C5 1.390(4) . ? C5 C6 1.390(5) . ? C6 C7 1.389(4) . ? C8 C9 1.401(3) . ? C8 C13 1.410(3) . ? C9 C10 1.394(3) . ? C10 C11 1.383(4) . ? C11 C12 1.389(4) . ? C12 C13 1.388(4) . ? C14 P3 1.834(3) . ? C15 P3 1.849(3) . ? C16 P3 1.839(3) . ? C17 P2 1.832(3) . ? C18 P2 1.825(3) . ? C19 P2 1.828(3) . ? C20 P1 1.831(3) . ? C21 P1 1.838(3) . ? C22 P1 1.838(3) . ? Co1 O1 1.8938(17) . ? Co1 P1 2.2043(7) . ? Co1 P2 2.2189(7) . ? Co1 P3 2.2492(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 C8 115.47(19) . . ? O1 C1 C2 113.38(18) . . ? C8 C1 C2 119.35(19) . . ? O1 C1 Co1 64.87(12) . . ? C8 C1 Co1 115.33(15) . . ? C2 C1 Co1 116.63(15) . . ? C3 C2 C7 115.5(2) . . ? C3 C2 C1 126.5(2) . . ? C7 C2 C1 117.9(2) . . ? F1 C3 C4 117.1(2) . . ? F1 C3 C2 119.1(2) . . ? C4 C3 C2 123.7(2) . . ? C3 C4 C5 119.0(3) . . ? C6 C5 C4 119.7(2) . . ? C7 C6 C5 119.9(3) . . ? C6 C7 C2 122.1(3) . . ? C9 C8 C13 117.2(2) . . ? C9 C8 C1 124.7(2) . . ? C13 C8 C1 118.0(2) . . ? C10 C9 C8 121.1(2) . . ? C11 C10 C9 120.9(3) . . ? C10 C11 C12 118.6(2) . . ? C13 C12 C11 121.1(3) . . ? C12 C13 C8 120.9(2) . . ? O1 Co1 C1 39.93(8) . . ? O1 Co1 P1 133.91(5) . . ? C1 Co1 P1 107.07(7) . . ? O1 Co1 P2 90.04(5) . . ? C1 Co1 P2 129.36(7) . . ? P1 Co1 P2 105.51(3) . . ? O1 Co1 P3 121.06(5) . . ? C1 Co1 P3 111.11(7) . . ? P1 Co1 P3 98.60(3) . . ? P2 Co1 P3 100.99(3) . . ? C1 O1 Co1 75.20(13) . . ? C20 P1 C21 99.70(18) . . ? C20 P1 C22 98.99(16) . . ? C21 P1 C22 100.90(18) . . ? C20 P1 Co1 119.53(10) . . ? C21 P1 Co1 115.43(11) . . ? C22 P1 Co1 118.78(10) . . ? C18 P2 C19 100.95(14) . . ? C18 P2 C17 100.20(15) . . ? C19 P2 C17 101.23(14) . . ? C18 P2 Co1 109.79(9) . . ? C19 P2 Co1 128.69(10) . . ? C17 P2 Co1 112.07(10) . . ? C14 P3 C16 99.78(14) . . ? C14 P3 C15 100.03(16) . . ? C16 P3 C15 98.80(14) . . ? C14 P3 Co1 115.10(10) . . ? C16 P3 Co1 117.47(10) . . ? C15 P3 Co1 121.87(10) . . ? 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 C1 C2 C3 -151.2(2) . . . . ? C8 C1 C2 C3 67.5(3) . . . . ? Co1 C1 C2 C3 -78.7(3) . . . . ? O1 C1 C2 C7 25.4(3) . . . . ? C8 C1 C2 C7 -115.9(2) . . . . ? Co1 C1 C2 C7 97.9(2) . . . . ? C7 C2 C3 F1 -177.1(2) . . . . ? C1 C2 C3 F1 -0.5(4) . . . . ? C7 C2 C3 C4 -0.3(4) . . . . ? C1 C2 C3 C4 176.3(2) . . . . ? F1 C3 C4 C5 177.4(2) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C4 C5 C6 C7 0.4(4) . . . . ? C5 C6 C7 C2 -0.2(4) . . . . ? C3 C2 C7 C6 0.2(4) . . . . ? C1 C2 C7 C6 -176.8(2) . . . . ? O1 C1 C8 C9 -174.0(2) . . . . ? C2 C1 C8 C9 -33.4(3) . . . . ? Co1 C1 C8 C9 113.2(2) . . . . ? O1 C1 C8 C13 5.9(3) . . . . ? C2 C1 C8 C13 146.5(2) . . . . ? Co1 C1 C8 C13 -66.9(3) . . . . ? C13 C8 C9 C10 3.3(3) . . . . ? C1 C8 C9 C10 -176.8(2) . . . . ? C8 C9 C10 C11 -3.0(4) . . . . ? C9 C10 C11 C12 0.4(4) . . . . ? C10 C11 C12 C13 1.8(4) . . . . ? C11 C12 C13 C8 -1.5(4) . . . . ? C9 C8 C13 C12 -1.1(4) . . . . ? C1 C8 C13 C12 179.0(2) . . . . ? C8 C1 Co1 O1 107.7(2) . . . . ? C2 C1 Co1 O1 -104.8(2) . . . . ? O1 C1 Co1 P1 -139.76(10) . . . . ? C8 C1 Co1 P1 -32.09(18) . . . . ? C2 C1 Co1 P1 115.46(16) . . . . ? O1 C1 Co1 P2 -11.90(14) . . . . ? C8 C1 Co1 P2 95.77(17) . . . . ? C2 C1 Co1 P2 -116.68(15) . . . . ? O1 C1 Co1 P3 113.61(10) . . . . ? C8 C1 Co1 P3 -138.72(15) . . . . ? C2 C1 Co1 P3 8.83(18) . . . . ? C8 C1 O1 Co1 -107.45(18) . . . . ? C2 C1 O1 Co1 109.66(18) . . . . ? P1 Co1 O1 C1 59.00(13) . . . . ? P2 Co1 O1 C1 170.83(11) . . . . ? P3 Co1 O1 C1 -86.29(12) . . . . ? O1 Co1 P1 C20 -76.02(15) . . . . ? C1 Co1 P1 C20 -40.89(15) . . . . ? P2 Co1 P1 C20 178.42(13) . . . . ? P3 Co1 P1 C20 74.42(13) . . . . ? O1 Co1 P1 C21 42.90(18) . . . . ? C1 Co1 P1 C21 78.04(17) . . . . ? P2 Co1 P1 C21 -62.65(16) . . . . ? P3 Co1 P1 C21 -166.66(16) . . . . ? O1 Co1 P1 C22 162.91(17) . . . . ? C1 Co1 P1 C22 -161.95(17) . . . . ? P2 Co1 P1 C22 57.36(15) . . . . ? P3 Co1 P1 C22 -46.65(15) . . . . ? O1 Co1 P2 C18 -48.67(12) . . . . ? C1 Co1 P2 C18 -41.06(14) . . . . ? P1 Co1 P2 C18 87.38(12) . . . . ? P3 Co1 P2 C18 -170.39(11) . . . . ? O1 Co1 P2 C19 -171.81(15) . . . . ? C1 Co1 P2 C19 -164.20(16) . . . . ? P1 Co1 P2 C19 -35.76(14) . . . . ? P3 Co1 P2 C19 66.47(14) . . . . ? O1 Co1 P2 C17 61.75(12) . . . . ? C1 Co1 P2 C17 69.36(14) . . . . ? P1 Co1 P2 C17 -162.20(11) . . . . ? P3 Co1 P2 C17 -59.97(12) . . . . ? O1 Co1 P3 C14 -9.60(13) . . . . ? C1 Co1 P3 C14 -52.96(13) . . . . ? P1 Co1 P3 C14 -165.08(11) . . . . ? P2 Co1 P3 C14 87.17(12) . . . . ? O1 Co1 P3 C16 -126.66(12) . . . . ? C1 Co1 P3 C16 -170.02(13) . . . . ? P1 Co1 P3 C16 77.86(11) . . . . ? P2 Co1 P3 C16 -29.90(11) . . . . ? O1 Co1 P3 C15 111.59(15) . . . . ? C1 Co1 P3 C15 68.23(16) . . . . ? P1 Co1 P3 C15 -43.89(14) . . . . ? P2 Co1 P3 C15 -151.64(14) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.717 _refine_diff_density_min -1.107 _refine_diff_density_rms 0.083 data_1 _database_code_depnum_ccdc_archive 'CCDC 678460' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H36 Co O P3' _chemical_formula_sum 'C22 H36 Co O P3' _chemical_formula_weight 468.35 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 Pna2(1) 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' _cell_length_a 16.4913(9) _cell_length_b 9.5041(5) _cell_length_c 15.8471(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2483.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.87 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.893 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.699 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_process_details 'SADABS (Bruker, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number 2144 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 460 _diffrn_standards_decay_% 0 _diffrn_reflns_number 23133 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5960 _reflns_number_gt 5407 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction 'SAINT (Bruker, 2002)' _computing_structure_solution 'SHELXTL (Bruker, 2002)' _computing_structure_refinement 'SHELXTL (Bruker, 2002)' _computing_molecular_graphics 'SHELXTL (Bruker, 2002)' _computing_publication_material 'SHELXTL (Bruker, 2002)' _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^)+(0.0418P)^2^+0.0155P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.005(9) _refine_ls_number_reflns 5960 _refine_ls_number_parameters 254 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0295 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0705 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Co1 Co 0.284934(12) 0.20354(2) 0.249346(17) 0.03456(7) Uani 1 1 d . . . P1 P 0.18097(4) 0.10228(5) 0.30855(3) 0.04856(13) Uani 1 1 d . . . P2 P 0.22640(3) 0.41113(5) 0.22159(4) 0.04420(12) Uani 1 1 d . . . P3 P 0.30103(3) 0.12831(5) 0.12012(3) 0.04615(12) Uani 1 1 d . . . O1 O 0.34233(8) 0.31652(12) 0.32868(8) 0.0394(3) Uani 1 1 d . . . C1 C 0.35561(12) 0.05811(18) 0.29265(13) 0.0441(4) Uani 1 1 d . . . C2 C 0.36620(16) -0.0840(2) 0.27078(15) 0.0594(6) Uani 1 1 d . . . H2A H 0.3319 -0.1234 0.2307 0.071 Uiso 1 1 calc R . . C3 C 0.42575(18) -0.1679(2) 0.30657(19) 0.0675(7) Uani 1 1 d . . . H3A H 0.4308 -0.2614 0.2902 0.081 Uiso 1 1 calc R . . C4 C 0.47772(16) -0.1125(2) 0.36667(18) 0.0651(6) Uani 1 1 d . . . H4A H 0.5191 -0.1676 0.3891 0.078 Uiso 1 1 calc R . . C5 C 0.46809(14) 0.0222(2) 0.39269(16) 0.0556(5) Uani 1 1 d . . . H5A H 0.5028 0.0585 0.4336 0.067 Uiso 1 1 calc R . . C6 C 0.40652(12) 0.10882(19) 0.35906(13) 0.0426(4) Uani 1 1 d . . . C7 C 0.39205(11) 0.2532(2) 0.37947(12) 0.0385(3) Uani 1 1 d . . . C8 C 0.42644(11) 0.3355(2) 0.44854(12) 0.0425(4) Uani 1 1 d . . . C9 C 0.45511(15) 0.2751(3) 0.52387(16) 0.0582(5) Uani 1 1 d . . . H9A H 0.4509 0.1785 0.5320 0.070 Uiso 1 1 calc R . . C10 C 0.48957(18) 0.3586(3) 0.58607(16) 0.0743(7) Uani 1 1 d . . . H10A H 0.5084 0.3170 0.6354 0.089 Uiso 1 1 calc R . . C11 C 0.49637(18) 0.5003(3) 0.57614(18) 0.0759(8) Uani 1 1 d . . . H11A H 0.5215 0.5545 0.6174 0.091 Uiso 1 1 calc R . . C12 C 0.46580(16) 0.5626(3) 0.50480(17) 0.0660(6) Uani 1 1 d . . . H12A H 0.4685 0.6598 0.4986 0.079 Uiso 1 1 calc R . . C13 C 0.43097(13) 0.4814(2) 0.44203(13) 0.0491(5) Uani 1 1 d . . . H13A H 0.4101 0.5254 0.3943 0.059 Uiso 1 1 calc R . . C14 C 0.1818(2) 0.1313(4) 0.42272(18) 0.0885(10) Uani 1 1 d . . . H14A H 0.1378 0.0808 0.4481 0.133 Uiso 1 1 calc R . . H14B H 0.1760 0.2300 0.4342 0.133 Uiso 1 1 calc R . . H14C H 0.2323 0.0985 0.4457 0.133 Uiso 1 1 calc R . . C15 C 0.1673(2) -0.0880(3) 0.3052(2) 0.0836(9) Uani 1 1 d . . . H15A H 0.2159 -0.1334 0.3243 0.125 Uiso 1 1 calc R . . H15B H 0.1558 -0.1167 0.2484 0.125 Uiso 1 1 calc R . . H15C H 0.1229 -0.1141 0.3412 0.125 Uiso 1 1 calc R . . C16 C 0.07733(15) 0.1559(3) 0.2814(2) 0.0745(7) Uani 1 1 d . . . H16A H 0.0395 0.0899 0.3049 0.112 Uiso 1 1 calc R . . H16B H 0.0714 0.1581 0.2212 0.112 Uiso 1 1 calc R . . H16C H 0.0668 0.2479 0.3040 0.112 Uiso 1 1 calc R . . C17 C 0.13822(19) 0.4418(4) 0.1535(2) 0.0898(10) Uani 1 1 d . . . H17A H 0.0964 0.3752 0.1670 0.135 Uiso 1 1 calc R . . H17B H 0.1538 0.4308 0.0955 0.135 Uiso 1 1 calc R . . H17C H 0.1182 0.5356 0.1624 0.135 Uiso 1 1 calc R . . C18 C 0.29832(18) 0.5412(3) 0.1813(2) 0.0729(7) Uani 1 1 d . . . H18A H 0.2712 0.6298 0.1739 0.109 Uiso 1 1 calc R . . H18B H 0.3195 0.5100 0.1281 0.109 Uiso 1 1 calc R . . H18C H 0.3420 0.5523 0.2208 0.109 Uiso 1 1 calc R . . C19 C 0.19386(19) 0.5006(3) 0.31776(19) 0.0692(7) Uani 1 1 d . . . H19A H 0.1790 0.5958 0.3047 0.104 Uiso 1 1 calc R . . H19B H 0.2375 0.5007 0.3579 0.104 Uiso 1 1 calc R . . H19C H 0.1480 0.4524 0.3413 0.104 Uiso 1 1 calc R . . C20 C 0.4060(2) 0.0882(4) 0.0903(2) 0.0921(10) Uani 1 1 d . . . H20A H 0.4080 0.0633 0.0316 0.138 Uiso 1 1 calc R . . H20B H 0.4255 0.0109 0.1236 0.138 Uiso 1 1 calc R . . H20C H 0.4394 0.1693 0.1000 0.138 Uiso 1 1 calc R . . C21 C 0.2493(2) -0.0319(3) 0.08431(16) 0.0716(7) Uani 1 1 d . . . H21A H 0.1918 -0.0202 0.0902 0.107 Uiso 1 1 calc R . . H21B H 0.2668 -0.1103 0.1178 0.107 Uiso 1 1 calc R . . H21C H 0.2623 -0.0489 0.0262 0.107 Uiso 1 1 calc R . . C22 C 0.2740(3) 0.2414(4) 0.03066(18) 0.0972(13) Uani 1 1 d . . . H22A H 0.2917 0.1982 -0.0209 0.146 Uiso 1 1 calc R . . H22B H 0.2998 0.3313 0.0369 0.146 Uiso 1 1 calc R . . H22C H 0.2162 0.2538 0.0291 0.146 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Co1 0.03988(11) 0.02942(10) 0.03437(11) -0.00029(9) -0.00291(11) -0.00017(8) P1 0.0583(3) 0.0449(2) 0.0425(3) -0.0004(2) 0.0092(2) -0.0113(2) P2 0.0482(3) 0.0358(2) 0.0486(3) 0.00171(18) -0.0053(2) 0.00494(17) P3 0.0587(3) 0.0421(2) 0.0377(2) -0.0029(2) 0.0061(2) -0.0004(2) O1 0.0444(7) 0.0341(6) 0.0398(7) -0.0014(5) -0.0063(5) -0.0012(5) C1 0.0503(10) 0.0342(8) 0.0476(10) 0.0017(8) -0.0063(8) 0.0040(7) C2 0.0761(15) 0.0387(9) 0.0636(15) -0.0027(8) -0.0189(11) 0.0050(9) C3 0.0877(18) 0.0386(10) 0.0763(16) -0.0005(11) -0.0082(14) 0.0138(10) C4 0.0686(14) 0.0529(12) 0.0739(16) 0.0103(11) -0.0155(13) 0.0167(11) C5 0.0535(12) 0.0513(11) 0.0621(13) 0.0071(9) -0.0120(10) 0.0057(9) C6 0.0434(9) 0.0405(9) 0.0438(10) 0.0054(7) -0.0040(8) -0.0009(7) C7 0.0375(9) 0.0403(8) 0.0376(9) 0.0032(7) -0.0011(7) -0.0014(7) C8 0.0368(9) 0.0534(10) 0.0374(9) -0.0041(8) 0.0014(7) -0.0037(8) C9 0.0609(14) 0.0702(14) 0.0435(12) 0.0046(9) -0.0055(10) -0.0005(11) C10 0.0705(16) 0.106(2) 0.0462(13) -0.0059(13) -0.0124(11) 0.0019(16) C11 0.0653(16) 0.100(2) 0.0626(16) -0.0366(14) -0.0085(12) -0.0097(14) C12 0.0657(15) 0.0662(13) 0.0662(16) -0.0240(12) 0.0042(12) -0.0112(12) C13 0.0520(11) 0.0521(11) 0.0431(10) -0.0089(8) 0.0022(8) -0.0059(8) C14 0.117(3) 0.106(2) 0.0427(13) 0.0034(14) 0.0180(16) -0.028(2) C15 0.102(2) 0.0537(13) 0.095(2) 0.0028(14) 0.0238(19) -0.0295(14) C16 0.0452(12) 0.0938(18) 0.0844(19) -0.0054(16) 0.0110(11) -0.0103(12) C17 0.0789(19) 0.089(2) 0.101(2) 0.0039(17) -0.0404(18) 0.0263(16) C18 0.0929(19) 0.0463(12) 0.0795(18) 0.0089(12) 0.0062(15) -0.0105(12) C19 0.0831(17) 0.0521(12) 0.0724(17) -0.0130(12) 0.0065(14) 0.0209(12) C20 0.0734(18) 0.107(2) 0.096(2) -0.0040(18) 0.0424(17) 0.0032(17) C21 0.099(2) 0.0603(13) 0.0554(15) -0.0123(11) -0.0138(14) -0.0124(15) C22 0.176(4) 0.0776(19) 0.0380(13) 0.0070(14) -0.0038(17) 0.022(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 Co1 O1 1.9051(12) . ? Co1 C1 1.9339(18) . ? Co1 P1 2.1786(6) . ? Co1 P3 2.1852(6) . ? Co1 P2 2.2401(5) . ? P1 C15 1.823(2) . ? P1 C14 1.830(3) . ? P1 C16 1.835(3) . ? P2 C19 1.826(3) . ? P2 C18 1.828(3) . ? P2 C17 1.834(3) . ? P3 C22 1.834(3) . ? P3 C20 1.835(3) . ? P3 C21 1.835(2) . ? O1 C7 1.297(2) . ? C1 C2 1.405(3) . ? C1 C6 1.430(3) . ? C2 C3 1.386(3) . ? C3 C4 1.385(4) . ? C4 C5 1.355(3) . ? C5 C6 1.411(3) . ? C6 C7 1.430(3) . ? C7 C8 1.460(3) . ? C8 C13 1.393(3) . ? C8 C9 1.407(3) . ? C9 C10 1.387(4) . ? C10 C11 1.360(4) . ? C11 C12 1.372(4) . ? C12 C13 1.384(3) . ? 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 C1 82.49(7) . . ? O1 Co1 P1 110.84(5) . . ? C1 Co1 P1 90.33(6) . . ? O1 Co1 P3 137.94(5) . . ? C1 Co1 P3 91.46(6) . . ? P1 Co1 P3 110.77(2) . . ? O1 Co1 P2 81.21(4) . . ? C1 Co1 P2 163.52(6) . . ? P1 Co1 P2 97.73(2) . . ? P3 Co1 P2 99.01(2) . . ? C15 P1 C14 100.32(16) . . ? C15 P1 C16 98.84(15) . . ? C14 P1 C16 101.36(17) . . ? C15 P1 Co1 121.54(10) . . ? C14 P1 Co1 110.66(11) . . ? C16 P1 Co1 120.63(10) . . ? C19 P2 C18 99.62(14) . . ? C19 P2 C17 100.60(15) . . ? C18 P2 C17 101.62(17) . . ? C19 P2 Co1 111.90(9) . . ? C18 P2 Co1 112.62(10) . . ? C17 P2 Co1 126.68(11) . . ? C22 P3 C20 98.76(19) . . ? C22 P3 C21 97.70(16) . . ? C20 P3 C21 100.74(16) . . ? C22 P3 Co1 120.21(11) . . ? C20 P3 Co1 115.09(13) . . ? C21 P3 Co1 120.32(10) . . ? C7 O1 Co1 117.51(11) . . ? C2 C1 C6 115.63(18) . . ? C2 C1 Co1 132.40(16) . . ? C6 C1 Co1 111.97(13) . . ? C3 C2 C1 122.7(2) . . ? C4 C3 C2 120.1(2) . . ? C5 C4 C3 119.7(2) . . ? C4 C5 C6 121.4(2) . . ? C5 C6 C7 126.45(18) . . ? C5 C6 C1 120.25(18) . . ? C7 C6 C1 113.08(16) . . ? O1 C7 C6 114.23(16) . . ? O1 C7 C8 117.51(17) . . ? C6 C7 C8 128.25(17) . . ? C13 C8 C9 116.84(18) . . ? C13 C8 C7 119.94(18) . . ? C9 C8 C7 123.22(19) . . ? C10 C9 C8 120.5(2) . . ? C11 C10 C9 121.2(2) . . ? C10 C11 C12 119.5(2) . . ? C11 C12 C13 120.3(2) . . ? C12 C13 C8 121.6(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 O1 Co1 P1 C15 -124.71(15) . . . . ? C1 Co1 P1 C15 -42.62(15) . . . . ? P3 Co1 P1 C15 49.06(15) . . . . ? P2 Co1 P1 C15 151.80(14) . . . . ? O1 Co1 P1 C14 -7.57(15) . . . . ? C1 Co1 P1 C14 74.52(15) . . . . ? P3 Co1 P1 C14 166.20(14) . . . . ? P2 Co1 P1 C14 -91.07(14) . . . . ? O1 Co1 P1 C16 110.33(13) . . . . ? C1 Co1 P1 C16 -167.58(13) . . . . ? P3 Co1 P1 C16 -75.90(12) . . . . ? P2 Co1 P1 C16 26.84(12) . . . . ? O1 Co1 P2 C19 -48.27(12) . . . . ? C1 Co1 P2 C19 -56.9(3) . . . . ? P1 Co1 P2 C19 61.75(12) . . . . ? P3 Co1 P2 C19 174.32(12) . . . . ? O1 Co1 P2 C18 62.98(13) . . . . ? C1 Co1 P2 C18 54.4(3) . . . . ? P1 Co1 P2 C18 173.00(12) . . . . ? P3 Co1 P2 C18 -74.43(12) . . . . ? O1 Co1 P2 C17 -171.40(17) . . . . ? C1 Co1 P2 C17 180.0(3) . . . . ? P1 Co1 P2 C17 -61.38(17) . . . . ? P3 Co1 P2 C17 51.19(17) . . . . ? O1 Co1 P3 C22 -82.77(19) . . . . ? C1 Co1 P3 C22 -163.16(19) . . . . ? P1 Co1 P3 C22 105.93(18) . . . . ? P2 Co1 P3 C22 4.06(18) . . . . ? O1 Co1 P3 C20 35.07(14) . . . . ? C1 Co1 P3 C20 -45.31(14) . . . . ? P1 Co1 P3 C20 -136.22(13) . . . . ? P2 Co1 P3 C20 121.91(13) . . . . ? O1 Co1 P3 C21 155.88(13) . . . . ? C1 Co1 P3 C21 75.50(13) . . . . ? P1 Co1 P3 C21 -15.41(13) . . . . ? P2 Co1 P3 C21 -117.28(13) . . . . ? C1 Co1 O1 C7 -7.14(14) . . . . ? P1 Co1 O1 C7 80.34(13) . . . . ? P3 Co1 O1 C7 -90.95(14) . . . . ? P2 Co1 O1 C7 175.31(13) . . . . ? O1 Co1 C1 C2 -176.7(2) . . . . ? P1 Co1 C1 C2 72.3(2) . . . . ? P3 Co1 C1 C2 -38.5(2) . . . . ? P2 Co1 C1 C2 -168.13(17) . . . . ? O1 Co1 C1 C6 2.65(15) . . . . ? P1 Co1 C1 C6 -108.34(15) . . . . ? P3 Co1 C1 C6 140.87(15) . . . . ? P2 Co1 C1 C6 11.2(3) . . . . ? C6 C1 C2 C3 -4.4(4) . . . . ? Co1 C1 C2 C3 174.9(2) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C2 C3 C4 C5 2.6(4) . . . . ? C3 C4 C5 C6 -0.8(4) . . . . ? C4 C5 C6 C7 -177.9(2) . . . . ? C4 C5 C6 C1 -3.7(4) . . . . ? C2 C1 C6 C5 6.1(3) . . . . ? Co1 C1 C6 C5 -173.39(17) . . . . ? C2 C1 C6 C7 -179.0(2) . . . . ? Co1 C1 C6 C7 1.5(2) . . . . ? Co1 O1 C7 C6 9.8(2) . . . . ? Co1 O1 C7 C8 -170.73(12) . . . . ? C5 C6 C7 O1 167.4(2) . . . . ? C1 C6 C7 O1 -7.2(2) . . . . ? C5 C6 C7 C8 -12.0(3) . . . . ? C1 C6 C7 C8 173.42(19) . . . . ? O1 C7 C8 C13 -23.5(3) . . . . ? C6 C7 C8 C13 155.9(2) . . . . ? O1 C7 C8 C9 155.6(2) . . . . ? C6 C7 C8 C9 -25.1(3) . . . . ? C13 C8 C9 C10 -3.0(3) . . . . ? C7 C8 C9 C10 177.9(2) . . . . ? C8 C9 C10 C11 0.2(4) . . . . ? C9 C10 C11 C12 2.6(5) . . . . ? C10 C11 C12 C13 -2.3(4) . . . . ? C11 C12 C13 C8 -0.6(4) . . . . ? C9 C8 C13 C12 3.2(3) . . . . ? C7 C8 C13 C12 -177.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.256 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.048