# 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 _publ_contact_author_name 'Fernando Godoy' _publ_contact_author_email FERNANDO.GODOY@USACH.CL _publ_section_title ; Synthesis, Reactivity and Molecular Structure of Phosphino Tetramethyl Cyclopentadienyl Complex (eta5:eta1-C5Me4CH2PPh2)Re(CO)2 ; loop_ _publ_author_name 'Fernando Godoy' 'Maria T Garland' 'Andres Ibanez' 'A Hugo Klahn' 'Juan Carlos Munoz' 'Beatriz Oelckers' ; R.N.Perutz ; data_6a _database_code_depnum_ccdc_archive 'CCDC 703987' _audit_update_record ; 2008-09-21 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 I2 O P Re' _chemical_formula_sum 'C23 H24 I2 O P Re' _chemical_formula_weight 787.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 15.1360(15) _cell_length_b 8.7980(8) _cell_length_c 17.9659(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.464(2) _cell_angle_gamma 90.00 _cell_volume 2326.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 990 _cell_measurement_theta_min 2.332 _cell_measurement_theta_max 18.70 _exptl_crystal_description Plates _exptl_crystal_colour Red _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 7.957 _exptl_absorpt_correction_T_min 0.36 _exptl_absorpt_correction_T_max 0.62 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS in SAINT-NT (Bruker, 2002)' _diffrn_ambient_temperature 273(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 'Bruker CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16711 _diffrn_reflns_av_R_equivalents 0.0811 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 28.10 _reflns_number_total 5271 _reflns_number_gt 3766 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART-NT (Bruker, 2001)' _computing_cell_refinement 'SAINT-NT (Bruker, 2000 )' _computing_data_reduction 'SAINT-NT (Bruker, 2000 )' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXS-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT (Sheldrick, 2000)' _computing_publication_material 'SHELXTL-NT (Sheldrick, 2000)' _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^)+(0.0397P)^2^+4.9482P] 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 5271 _refine_ls_number_parameters 262 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1194 _refine_ls_wR_factor_gt 0.1088 _refine_ls_goodness_of_fit_ref 1.045 _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 Re1 Re -0.00653(3) 0.94596(4) 0.76561(2) 0.03023(13) Uani 1 1 d . . . I1 I 0.09638(5) 1.21082(8) 0.79712(5) 0.0515(2) Uani 1 1 d . . . I2 I -0.14816(5) 1.15565(9) 0.73264(5) 0.0522(2) Uani 1 1 d . . . P1 P 0.12236(18) 0.8253(3) 0.85209(15) 0.0325(6) Uani 1 1 d . . . C1 C 0.0612(7) 0.7562(10) 0.7151(6) 0.032(2) Uani 1 1 d . . . C2 C -0.0302(7) 0.7141(11) 0.7097(6) 0.038(2) Uani 1 1 d . . . C3 C -0.0826(7) 0.8228(11) 0.6602(6) 0.039(3) Uani 1 1 d . . . C4 C -0.0248(7) 0.9287(12) 0.6341(6) 0.042(3) Uani 1 1 d . . . C5 C 0.0654(8) 0.8889(12) 0.6675(6) 0.040(3) Uani 1 1 d . . . C6 C -0.0634(8) 0.5731(12) 0.7409(8) 0.058(3) Uani 1 1 d . . . H6A H -0.0787 0.4983 0.7010 0.088 Uiso 1 1 calc R . . H6B H -0.1161 0.5965 0.7597 0.088 Uiso 1 1 calc R . . H6C H -0.0165 0.5339 0.7819 0.088 Uiso 1 1 calc R . . C7 C -0.1840(8) 0.8070(15) 0.6288(7) 0.064(4) Uani 1 1 d . . . H7A H -0.1953 0.7374 0.5865 0.095 Uiso 1 1 calc R . . H7B H -0.2094 0.9044 0.6119 0.095 Uiso 1 1 calc R . . H7C H -0.2114 0.7691 0.6682 0.095 Uiso 1 1 calc R . . C8 C -0.0558(9) 1.0502(15) 0.5764(7) 0.068(4) Uani 1 1 d . . . H8A H -0.0743 1.0056 0.5264 0.102 Uiso 1 1 calc R . . H8B H -0.0070 1.1203 0.5773 0.102 Uiso 1 1 calc R . . H8C H -0.1062 1.1033 0.5883 0.102 Uiso 1 1 calc R . . C9 C 0.1522(7) 0.9567(13) 0.6525(7) 0.049(3) Uani 1 1 d . . . H9A H 0.1690 0.9024 0.6116 0.074 Uiso 1 1 calc R . . H9B H 0.2001 0.9488 0.6980 0.074 Uiso 1 1 calc R . . H9C H 0.1422 1.0618 0.6386 0.074 Uiso 1 1 calc R . . C10 C 0.1421(7) 0.6999(12) 0.7762(6) 0.038(2) Uani 1 1 d . . . H10A H 0.1997 0.7195 0.7631 0.046 Uiso 1 1 calc R . . H10B H 0.1372 0.5932 0.7882 0.046 Uiso 1 1 calc R . . C11 C 0.2294(7) 0.9229(11) 0.8941(6) 0.040(3) Uani 1 1 d . . . C12 C 0.3037(7) 0.9124(12) 0.8673(7) 0.045(3) Uani 1 1 d . . . H12 H 0.3022 0.8534 0.8241 0.055 Uiso 1 1 calc R . . C13 C 0.3835(8) 0.9865(15) 0.9017(7) 0.057(3) Uani 1 1 d . . . H13 H 0.4352 0.9764 0.8825 0.068 Uiso 1 1 calc R . . C14 C 0.3846(10) 1.0753(15) 0.9648(9) 0.070(4) Uani 1 1 d . . . H14 H 0.4369 1.1293 0.9873 0.084 Uiso 1 1 calc R . . C15 C 0.3107(10) 1.0851(14) 0.9945(8) 0.068(4) Uani 1 1 d . . . H15 H 0.3131 1.1410 1.0389 0.081 Uiso 1 1 calc R . . C16 C 0.2309(8) 1.0115(13) 0.9586(7) 0.054(3) Uani 1 1 d . . . H16 H 0.1789 1.0214 0.9775 0.065 Uiso 1 1 calc R . . C17 C 0.1077(7) 0.7064(11) 0.9306(6) 0.037(2) Uani 1 1 d . . . C18 C 0.1416(8) 0.5620(13) 0.9405(7) 0.048(3) Uani 1 1 d . . . H18 H 0.1672 0.5197 0.9030 0.057 Uiso 1 1 calc R . . C19 C 0.1390(9) 0.4779(14) 1.0037(8) 0.057(3) Uani 1 1 d . . . H19 H 0.1616 0.3791 1.0089 0.069 Uiso 1 1 calc R . . C20 C 0.1024(9) 0.5419(18) 1.0597(8) 0.071(4) Uani 1 1 d . . . H20 H 0.0993 0.4850 1.1026 0.085 Uiso 1 1 calc R . . C21 C 0.0704(9) 0.6880(18) 1.0530(7) 0.066(4) Uani 1 1 d . . . H21 H 0.0478 0.7308 1.0921 0.079 Uiso 1 1 calc R . . C22 C 0.0718(8) 0.7721(14) 0.9881(6) 0.049(3) Uani 1 1 d . . . H22 H 0.0491 0.8708 0.9828 0.059 Uiso 1 1 calc R . . C23 C -0.0730(8) 0.8988(12) 0.8379(6) 0.059(4) Uani 1 1 d D . . O1 O -0.1186(4) 0.8657(7) 0.8731(4) 0.0276(15) Uani 1 1 d 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 Re1 0.0296(2) 0.0285(2) 0.0335(2) -0.00118(18) 0.00911(17) 0.00181(17) I1 0.0524(5) 0.0364(4) 0.0664(6) -0.0021(4) 0.0149(4) -0.0024(3) I2 0.0427(4) 0.0473(5) 0.0661(6) -0.0015(4) 0.0117(4) 0.0149(4) P1 0.0324(14) 0.0331(14) 0.0313(15) -0.0010(11) 0.0061(12) 0.0010(11) C1 0.043(6) 0.024(5) 0.034(6) -0.008(4) 0.016(5) 0.002(4) C2 0.045(6) 0.037(6) 0.034(6) -0.008(5) 0.015(5) -0.004(5) C3 0.035(6) 0.036(6) 0.045(7) -0.016(5) 0.007(5) -0.004(5) C4 0.039(6) 0.052(7) 0.033(6) 0.004(5) 0.004(5) 0.014(5) C5 0.049(7) 0.042(6) 0.031(6) -0.004(5) 0.014(5) 0.004(5) C6 0.059(8) 0.045(7) 0.080(10) -0.003(6) 0.033(7) -0.003(6) C7 0.042(7) 0.085(10) 0.056(8) -0.016(7) -0.002(6) 0.007(7) C8 0.069(9) 0.093(10) 0.045(8) 0.018(7) 0.020(7) 0.034(8) C9 0.044(7) 0.055(7) 0.053(7) -0.005(6) 0.021(6) -0.006(6) C10 0.033(6) 0.041(6) 0.042(6) -0.004(5) 0.012(5) 0.000(5) C11 0.041(6) 0.034(6) 0.045(7) -0.001(5) 0.008(5) -0.008(5) C12 0.041(7) 0.043(7) 0.052(7) -0.011(5) 0.008(6) -0.012(5) C13 0.047(8) 0.069(9) 0.051(8) 0.012(7) 0.006(6) -0.007(6) C14 0.057(9) 0.058(9) 0.085(11) -0.004(8) -0.003(8) -0.005(7) C15 0.067(10) 0.046(8) 0.077(10) -0.017(7) -0.008(8) -0.006(7) C16 0.047(7) 0.053(7) 0.056(8) -0.010(6) 0.002(6) -0.007(6) C17 0.035(6) 0.036(6) 0.035(6) 0.003(5) -0.001(5) -0.009(5) C18 0.048(7) 0.047(7) 0.047(7) 0.004(6) 0.010(6) -0.010(6) C19 0.055(8) 0.052(8) 0.061(9) 0.007(7) 0.006(7) -0.013(6) C20 0.049(8) 0.098(12) 0.054(9) 0.028(9) -0.012(7) -0.032(8) C21 0.058(9) 0.105(12) 0.038(8) -0.003(8) 0.015(6) -0.016(8) C22 0.045(7) 0.059(8) 0.045(7) -0.008(6) 0.012(6) -0.006(6) C23 0.058(9) 0.035(7) 0.064(9) -0.019(6) -0.024(7) 0.021(6) O1 0.009(3) 0.034(4) 0.044(4) -0.004(3) 0.014(3) 0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C23 1.865(11) . ? Re1 C3 2.252(10) . ? Re1 C1 2.257(9) . ? Re1 C2 2.265(10) . ? Re1 C4 2.319(10) . ? Re1 C5 2.331(10) . ? Re1 P1 2.436(3) . ? Re1 I2 2.7855(8) . ? Re1 I1 2.7868(9) . ? P1 C17 1.810(10) . ? P1 C10 1.832(10) . ? P1 C11 1.834(11) . ? C1 C2 1.414(14) . ? C1 C5 1.458(14) . ? C1 C10 1.524(14) . ? C2 C3 1.416(14) . ? C2 C6 1.496(14) . ? C3 C4 1.430(14) . ? C3 C7 1.513(15) . ? C4 C5 1.401(14) . ? C4 C8 1.487(15) . ? C5 C9 1.523(14) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.325(15) . ? C11 C16 1.393(15) . ? C12 C13 1.385(15) . ? C12 H12 0.9300 . ? C13 C14 1.374(17) . ? C13 H13 0.9300 . ? C14 C15 1.350(19) . ? C14 H14 0.9300 . ? C15 C16 1.389(16) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.366(14) . ? C17 C22 1.400(14) . ? C18 C19 1.364(15) . ? C18 H18 0.9300 . ? C19 C20 1.376(19) . ? C19 H19 0.9300 . ? C20 C21 1.369(19) . ? C20 H20 0.9300 . ? C21 C22 1.386(16) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? C23 O1 1.080(9) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 Re1 C3 103.0(5) . . ? C23 Re1 C1 119.0(4) . . ? C3 Re1 C1 59.8(4) . . ? C23 Re1 C2 93.1(4) . . ? C3 Re1 C2 36.5(4) . . ? C1 Re1 C2 36.4(4) . . ? C23 Re1 C4 137.7(5) . . ? C3 Re1 C4 36.4(4) . . ? C1 Re1 C4 60.0(4) . . ? C2 Re1 C4 61.3(4) . . ? C23 Re1 C5 154.3(4) . . ? C3 Re1 C5 59.9(4) . . ? C1 Re1 C5 37.0(3) . . ? C2 Re1 C5 61.6(4) . . ? C4 Re1 C5 35.1(4) . . ? C23 Re1 P1 86.6(4) . . ? C3 Re1 P1 120.2(3) . . ? C1 Re1 P1 64.1(3) . . ? C2 Re1 P1 84.9(3) . . ? C4 Re1 P1 120.6(3) . . ? C5 Re1 P1 86.7(3) . . ? C23 Re1 I2 77.4(3) . . ? C3 Re1 I2 85.5(3) . . ? C1 Re1 I2 143.5(3) . . ? C2 Re1 I2 117.9(3) . . ? C4 Re1 I2 85.6(3) . . ? C5 Re1 I2 117.0(3) . . ? P1 Re1 I2 152.44(7) . . ? C23 Re1 I1 114.3(3) . . ? C3 Re1 I1 136.5(3) . . ? C1 Re1 I1 114.6(3) . . ? C2 Re1 I1 150.0(3) . . ? C4 Re1 I1 101.0(3) . . ? C5 Re1 I1 89.8(3) . . ? P1 Re1 I1 84.73(7) . . ? I2 Re1 I1 81.69(3) . . ? C17 P1 C10 107.6(5) . . ? C17 P1 C11 101.9(5) . . ? C10 P1 C11 107.9(5) . . ? C17 P1 Re1 121.6(3) . . ? C10 P1 Re1 91.9(3) . . ? C11 P1 Re1 123.9(3) . . ? C2 C1 C5 110.1(9) . . ? C2 C1 C10 125.1(9) . . ? C5 C1 C10 123.1(9) . . ? C2 C1 Re1 72.1(5) . . ? C5 C1 Re1 74.3(5) . . ? C10 C1 Re1 108.4(6) . . ? C3 C2 C1 105.2(9) . . ? C3 C2 C6 127.5(10) . . ? C1 C2 C6 126.8(10) . . ? C3 C2 Re1 71.2(6) . . ? C1 C2 Re1 71.5(5) . . ? C6 C2 Re1 127.8(7) . . ? C2 C3 C4 110.5(9) . . ? C2 C3 C7 122.8(10) . . ? C4 C3 C7 125.6(10) . . ? C2 C3 Re1 72.3(6) . . ? C4 C3 Re1 74.4(6) . . ? C7 C3 Re1 129.3(8) . . ? C5 C4 C3 107.8(9) . . ? C5 C4 C8 126.6(11) . . ? C3 C4 C8 125.4(10) . . ? C5 C4 Re1 72.9(6) . . ? C3 C4 Re1 69.2(6) . . ? C8 C4 Re1 127.3(8) . . ? C4 C5 C1 106.3(9) . . ? C4 C5 C9 128.4(10) . . ? C1 C5 C9 125.1(10) . . ? C4 C5 Re1 72.0(6) . . ? C1 C5 Re1 68.7(5) . . ? C9 C5 Re1 128.5(7) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 P1 95.6(6) . . ? C1 C10 H10A 112.6 . . ? P1 C10 H10A 112.6 . . ? C1 C10 H10B 112.6 . . ? P1 C10 H10B 112.6 . . ? H10A C10 H10B 110.1 . . ? C12 C11 C16 119.4(10) . . ? C12 C11 P1 124.1(9) . . ? C16 C11 P1 116.5(9) . . ? C11 C12 C13 122.0(11) . . ? C11 C12 H12 119.0 . . ? C13 C12 H12 119.0 . . ? C14 C13 C12 118.6(13) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 120.6(13) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 119.9(14) . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C11 C16 C15 119.4(12) . . ? C11 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C18 C17 C22 119.1(10) . . ? C18 C17 P1 121.9(9) . . ? C22 C17 P1 118.4(8) . . ? C19 C18 C17 122.1(12) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C18 C19 C20 118.7(13) . . ? C18 C19 H19 120.6 . . ? C20 C19 H19 120.6 . . ? C21 C20 C19 121.0(13) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 120.1(13) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C17 119.0(12) . . ? C21 C22 H22 120.5 . . ? C17 C22 H22 120.5 . . ? O1 C23 Re1 172.0(11) . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.690 _refine_diff_density_min -1.097 _refine_diff_density_rms 0.223 data_3a _database_code_depnum_ccdc_archive 'CCDC 703988' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 O2 P Re' _chemical_formula_sum 'C24 H24 O2 P Re' _chemical_formula_weight 561.60 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' Re Re -1.0185 7.2310 '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 _symmetry_space_group_name_Hall '-P 2yn' 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 9.7394(5) _cell_length_b 21.5708(11) _cell_length_c 10.2864(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.6850(10) _cell_angle_gamma 90.00 _cell_volume 2108.29(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 943 _cell_measurement_theta_min 2.238 _cell_measurement_theta_max 28.00 _exptl_crystal_description blocks _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.769 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 5.856 _exptl_absorpt_correction_type 'multi scans' _exptl_absorpt_correction_T_min 0.111 _exptl_absorpt_correction_T_max 0.276 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12358 _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.05 _reflns_number_total 5121 _reflns_number_gt 4002 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART-NT (Bruker, 2001)' _computing_cell_refinement 'SAINT-NT (Bruker, 2000 )' _computing_data_reduction 'SAINT-NT (Bruker, 2000 )' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT (Sheldrick, 2000)' _computing_publication_material 'SHELXTL-NT (Sheldrick, 2000)' _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^)+(0.0273P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4710 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0271 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0534 _refine_ls_wR_factor_gt 0.0521 _refine_ls_goodness_of_fit_ref 0.997 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Re1 Re 0.164859(12) 0.925385(6) 0.331124(11) 0.03374(5) Uani 1 1 d . . . P1 P 0.24187(8) 0.83224(4) 0.25954(7) 0.03600(18) Uani 1 1 d . . . O1 O -0.0059(3) 0.86436(14) 0.5118(2) 0.0626(7) Uani 1 1 d . . . O2 O 0.3857(3) 0.96626(14) 0.5750(3) 0.0686(8) Uani 1 1 d . . . C1 C 0.1364(3) 0.92182(14) 0.1073(3) 0.0375(7) Uani 1 1 d . . . C2 C 0.0011(3) 0.93262(15) 0.1350(3) 0.0402(8) Uani 1 1 d . . . C3 C 0.0068(3) 0.99109(16) 0.2013(3) 0.0432(8) Uani 1 1 d . . . C4 C 0.1443(3) 1.01624(15) 0.2138(3) 0.0426(8) Uani 1 1 d . . . C5 C 0.2264(3) 0.97309(15) 0.1544(3) 0.0399(7) Uani 1 1 d . . . C6 C -0.1261(3) 0.89169(19) 0.0959(3) 0.0536(9) Uani 1 1 d . . . H6A H -0.1791 0.9037 0.0096 0.080 Uiso 1 1 calc R . . H6B H -0.1838 0.8959 0.1601 0.080 Uiso 1 1 calc R . . H6C H -0.0967 0.8493 0.0932 0.080 Uiso 1 1 calc R . . C7 C -0.1171(4) 1.02374(19) 0.2358(4) 0.0615(10) Uani 1 1 d . . . H7A H -0.1640 1.0482 0.1611 0.092 Uiso 1 1 calc R . . H7B H -0.0850 1.0503 0.3113 0.092 Uiso 1 1 calc R . . H7C H -0.1814 0.9936 0.2569 0.092 Uiso 1 1 calc R . . C8 C 0.1945(5) 1.07862(16) 0.2693(4) 0.0624(11) Uani 1 1 d . . . H8A H 0.1726 1.1092 0.2001 0.094 Uiso 1 1 calc R . . H8B H 0.2945 1.0774 0.3035 0.094 Uiso 1 1 calc R . . H8C H 0.1486 1.0892 0.3399 0.094 Uiso 1 1 calc R . . C9 C 0.3712(3) 0.98458(18) 0.1333(3) 0.0529(9) Uani 1 1 d . . . H9A H 0.3651 1.0055 0.0498 0.079 Uiso 1 1 calc R . . H9B H 0.4190 0.9457 0.1320 0.079 Uiso 1 1 calc R . . H9C H 0.4225 1.0099 0.2043 0.079 Uiso 1 1 calc R . . C10 C 0.1921(3) 0.85775(15) 0.0831(3) 0.0425(8) Uani 1 1 d . . . H10A H 0.2726 0.8599 0.0420 0.051 Uiso 1 1 calc R . . H10B H 0.1198 0.8316 0.0302 0.051 Uiso 1 1 calc R . . C11 C 0.1455(3) 0.76161(15) 0.2759(3) 0.0393(7) Uani 1 1 d . . . C12 C 0.0639(4) 0.72927(17) 0.1698(4) 0.0514(9) Uani 1 1 d . . . H12A H 0.0618 0.7422 0.0832 0.062 Uiso 1 1 calc R . . C13 C -0.0140(4) 0.67838(18) 0.1904(4) 0.0601(10) Uani 1 1 d . . . H13A H -0.0679 0.6573 0.1180 0.072 Uiso 1 1 calc R . . C14 C -0.0123(4) 0.65861(17) 0.3174(4) 0.0570(10) Uani 1 1 d . . . H14A H -0.0654 0.6244 0.3311 0.068 Uiso 1 1 calc R . . C15 C 0.0678(4) 0.68944(17) 0.4243(4) 0.0539(9) Uani 1 1 d . . . H15A H 0.0696 0.6758 0.5104 0.065 Uiso 1 1 calc R . . C16 C 0.1456(4) 0.74056(16) 0.4045(3) 0.0476(8) Uani 1 1 d . . . H16A H 0.1989 0.7613 0.4777 0.057 Uiso 1 1 calc R . . C17 C 0.4259(3) 0.80870(15) 0.2888(3) 0.0395(7) Uani 1 1 d . . . C18 C 0.4662(4) 0.75142(17) 0.2477(3) 0.0487(8) Uani 1 1 d . . . H18A H 0.3981 0.7231 0.2070 0.058 Uiso 1 1 calc R . . C19 C 0.6077(4) 0.73644(19) 0.2671(4) 0.0567(10) Uani 1 1 d . . . H19A H 0.6346 0.6980 0.2401 0.068 Uiso 1 1 calc R . . C20 C 0.7085(4) 0.7786(2) 0.3267(4) 0.0604(10) Uani 1 1 d . . . H20A H 0.8034 0.7686 0.3395 0.073 Uiso 1 1 calc R . . C21 C 0.6694(3) 0.8354(2) 0.3670(4) 0.0595(10) Uani 1 1 d . . . H21A H 0.7376 0.8637 0.4071 0.071 Uiso 1 1 calc R . . C22 C 0.5273(3) 0.85034(17) 0.3476(3) 0.0486(9) Uani 1 1 d . . . H22A H 0.5008 0.8888 0.3747 0.058 Uiso 1 1 calc R . . C23 C 0.0602(3) 0.88852(16) 0.4460(3) 0.0413(8) Uani 1 1 d . . . C24 C 0.3041(4) 0.94924(17) 0.4835(3) 0.0436(8) 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 Re1 0.03460(7) 0.03593(8) 0.03045(8) -0.00257(5) 0.00661(5) 0.00057(5) P1 0.0365(4) 0.0364(5) 0.0349(4) -0.0015(4) 0.0074(3) 0.0009(3) O1 0.0581(15) 0.077(2) 0.0606(16) 0.0025(14) 0.0298(13) -0.0137(14) O2 0.0593(16) 0.081(2) 0.0559(16) -0.0192(15) -0.0089(13) -0.0125(15) C1 0.0436(17) 0.042(2) 0.0260(15) 0.0014(13) 0.0057(13) 0.0018(14) C2 0.0387(16) 0.046(2) 0.0329(16) 0.0043(14) 0.0019(13) 0.0034(14) C3 0.0451(17) 0.048(2) 0.0354(16) 0.0010(15) 0.0067(14) 0.0095(15) C4 0.0554(19) 0.0348(19) 0.0388(17) 0.0026(14) 0.0130(15) 0.0030(15) C5 0.0495(18) 0.0385(19) 0.0335(16) -0.0005(14) 0.0127(14) -0.0041(15) C6 0.0450(19) 0.064(3) 0.048(2) 0.0004(19) 0.0018(16) -0.0044(17) C7 0.057(2) 0.069(3) 0.058(2) -0.003(2) 0.0103(18) 0.022(2) C8 0.093(3) 0.042(2) 0.059(2) -0.0071(18) 0.032(2) -0.006(2) C9 0.0508(19) 0.059(3) 0.051(2) -0.0015(18) 0.0168(17) -0.0039(17) C10 0.0514(18) 0.042(2) 0.0352(17) -0.0048(14) 0.0114(14) 0.0011(15) C11 0.0397(16) 0.0335(18) 0.0441(17) -0.0032(15) 0.0081(14) 0.0027(13) C12 0.061(2) 0.043(2) 0.049(2) -0.0053(17) 0.0087(17) -0.0051(17) C13 0.062(2) 0.047(2) 0.068(3) -0.015(2) 0.007(2) -0.0111(18) C14 0.048(2) 0.039(2) 0.088(3) 0.000(2) 0.024(2) -0.0036(16) C15 0.057(2) 0.048(2) 0.061(2) 0.0104(19) 0.0215(19) 0.0060(18) C16 0.0471(18) 0.045(2) 0.050(2) 0.0000(16) 0.0084(16) -0.0002(15) C17 0.0393(16) 0.042(2) 0.0380(17) 0.0039(14) 0.0106(14) 0.0030(14) C18 0.0486(19) 0.046(2) 0.051(2) -0.0019(17) 0.0109(16) 0.0032(16) C19 0.060(2) 0.053(3) 0.061(2) 0.0020(19) 0.0214(19) 0.0179(19) C20 0.0431(18) 0.081(3) 0.060(2) 0.008(2) 0.0160(17) 0.019(2) C21 0.0433(19) 0.075(3) 0.059(2) -0.005(2) 0.0102(17) -0.0012(18) C22 0.0425(18) 0.052(2) 0.050(2) -0.0069(17) 0.0085(16) 0.0029(16) C23 0.0362(16) 0.048(2) 0.0388(17) -0.0052(15) 0.0056(14) 0.0006(14) C24 0.0482(18) 0.043(2) 0.0400(18) -0.0049(16) 0.0097(16) -0.0002(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Re1 C23 1.896(3) . ? Re1 C24 1.905(3) . ? Re1 C1 2.259(3) . ? Re1 C5 2.280(3) . ? Re1 C2 2.286(3) . ? Re1 C4 2.287(3) . ? Re1 C3 2.293(3) . ? Re1 P1 2.3204(8) . ? P1 C11 1.816(3) . ? P1 C17 1.824(3) . ? P1 C10 1.856(3) . ? O1 C23 1.156(4) . ? O2 C24 1.151(4) . ? C1 C2 1.427(4) . ? C1 C5 1.428(4) . ? C1 C10 1.525(4) . ? C2 C3 1.429(4) . ? C2 C6 1.503(5) . ? C3 C4 1.425(4) . ? C3 C7 1.505(4) . ? C4 C5 1.446(4) . ? C4 C8 1.501(4) . ? C5 C9 1.494(4) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.389(4) . ? C11 C16 1.399(5) . ? C12 C13 1.377(5) . ? C12 H12A 0.9300 . ? C13 C14 1.371(5) . ? C13 H13A 0.9300 . ? C14 C15 1.373(5) . ? C14 H14A 0.9300 . ? C15 C16 1.378(5) . ? C15 H15A 0.9300 . ? C16 H16A 0.9300 . ? C17 C22 1.373(4) . ? C17 C18 1.390(4) . ? C18 C19 1.387(5) . ? C18 H18A 0.9300 . ? C19 C20 1.379(6) . ? C19 H19A 0.9300 . ? C20 C21 1.372(6) . ? C20 H20A 0.9300 . ? C21 C22 1.393(4) . ? C21 H21A 0.9300 . ? C22 H22A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C23 Re1 C24 89.08(14) . . ? C23 Re1 C1 131.17(12) . . ? C24 Re1 C1 138.90(13) . . ? C23 Re1 C5 163.15(12) . . ? C24 Re1 C5 105.64(13) . . ? C1 Re1 C5 36.67(11) . . ? C23 Re1 C2 102.24(12) . . ? C24 Re1 C2 160.16(14) . . ? C1 Re1 C2 36.60(11) . . ? C5 Re1 C2 61.33(11) . . ? C23 Re1 C4 133.74(13) . . ? C24 Re1 C4 99.59(14) . . ? C1 Re1 C4 60.95(11) . . ? C5 Re1 C4 36.92(11) . . ? C2 Re1 C4 60.83(11) . . ? C23 Re1 C3 103.76(12) . . ? C24 Re1 C3 125.31(13) . . ? C1 Re1 C3 60.73(11) . . ? C5 Re1 C3 61.13(11) . . ? C2 Re1 C3 36.37(11) . . ? C4 Re1 C3 36.24(11) . . ? C23 Re1 P1 95.17(10) . . ? C24 Re1 P1 105.88(11) . . ? C1 Re1 P1 67.85(8) . . ? C5 Re1 P1 88.74(8) . . ? C2 Re1 P1 89.46(8) . . ? C4 Re1 P1 124.84(8) . . ? C3 Re1 P1 124.94(8) . . ? C11 P1 C17 105.10(15) . . ? C11 P1 C10 108.05(15) . . ? C17 P1 C10 106.27(15) . . ? C11 P1 Re1 119.16(10) . . ? C17 P1 Re1 124.29(11) . . ? C10 P1 Re1 91.16(10) . . ? C2 C1 C5 109.3(3) . . ? C2 C1 C10 123.9(3) . . ? C5 C1 C10 122.9(3) . . ? C2 C1 Re1 72.72(17) . . ? C5 C1 Re1 72.47(17) . . ? C10 C1 Re1 103.21(19) . . ? C1 C2 C3 107.4(3) . . ? C1 C2 C6 126.5(3) . . ? C3 C2 C6 126.1(3) . . ? C1 C2 Re1 70.68(17) . . ? C3 C2 Re1 72.10(18) . . ? C6 C2 Re1 124.8(2) . . ? C4 C3 C2 108.4(3) . . ? C4 C3 C7 126.0(3) . . ? C2 C3 C7 125.2(3) . . ? C4 C3 Re1 71.64(18) . . ? C2 C3 Re1 71.53(18) . . ? C7 C3 Re1 128.5(2) . . ? C3 C4 C5 108.2(3) . . ? C3 C4 C8 126.6(3) . . ? C5 C4 C8 125.0(3) . . ? C3 C4 Re1 72.12(19) . . ? C5 C4 Re1 71.28(18) . . ? C8 C4 Re1 125.7(2) . . ? C1 C5 C4 106.7(3) . . ? C1 C5 C9 127.4(3) . . ? C4 C5 C9 125.6(3) . . ? C1 C5 Re1 70.86(17) . . ? C4 C5 Re1 71.80(17) . . ? C9 C5 Re1 127.8(2) . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 H9A 109.5 . . ? C5 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C5 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 P1 97.78(19) . . ? C1 C10 H10A 112.2 . . ? P1 C10 H10A 112.2 . . ? C1 C10 H10B 112.2 . . ? P1 C10 H10B 112.2 . . ? H10A C10 H10B 109.8 . . ? C12 C11 C16 117.5(3) . . ? C12 C11 P1 124.5(3) . . ? C16 C11 P1 117.8(3) . . ? C13 C12 C11 121.3(3) . . ? C13 C12 H12A 119.4 . . ? C11 C12 H12A 119.4 . . ? C14 C13 C12 120.2(3) . . ? C14 C13 H13A 119.9 . . ? C12 C13 H13A 119.9 . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14A 120.1 . . ? C15 C14 H14A 120.1 . . ? C14 C15 C16 120.2(4) . . ? C14 C15 H15A 119.9 . . ? C16 C15 H15A 119.9 . . ? C15 C16 C11 120.9(3) . . ? C15 C16 H16A 119.6 . . ? C11 C16 H16A 119.6 . . ? C22 C17 C18 119.5(3) . . ? C22 C17 P1 118.4(3) . . ? C18 C17 P1 122.0(3) . . ? C19 C18 C17 120.1(3) . . ? C19 C18 H18A 120.0 . . ? C17 C18 H18A 120.0 . . ? C20 C19 C18 119.9(4) . . ? C20 C19 H19A 120.1 . . ? C18 C19 H19A 120.1 . . ? C21 C20 C19 120.3(3) . . ? C21 C20 H20A 119.8 . . ? C19 C20 H20A 119.8 . . ? C20 C21 C22 119.8(4) . . ? C20 C21 H21A 120.1 . . ? C22 C21 H21A 120.1 . . ? C17 C22 C21 120.5(3) . . ? C17 C22 H22A 119.8 . . ? C21 C22 H22A 119.8 . . ? O1 C23 Re1 177.2(3) . . ? O2 C24 Re1 176.9(3) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8C O1 0.96 2.49 3.431(5) 167 3_576 C21 H21A O1 0.93 2.49 3.247(4) 138 1_655 _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.314 _refine_diff_density_min -0.910 _refine_diff_density_rms 0.129