# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Fairlamb, Ian' _publ_contact_author_email ijsf1@york.ac.uk _publ_section_title ; Pd-catalyzed regioselective C-H functionalisation of 2-pyrones ; loop_ _publ_author_name M.Burns R.Thatcher R.Taylor I.Fairlamb # Attachment '- ijf0925m.cif' data_ijf0925m _database_code_depnum_ccdc_archive 'CCDC 764708' #TrackingRef '- ijf0925m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 O3' _chemical_formula_sum 'C12 H8 O3' _chemical_formula_weight 200.18 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1467(5) _cell_length_b 7.3546(5) _cell_length_c 9.3252(6) _cell_angle_alpha 69.7600(10) _cell_angle_beta 81.8920(10) _cell_angle_gamma 75.2200(10) _cell_volume 443.91(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4450 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.35 _exptl_crystal_description blocks _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.498 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 208 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.900 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details 'SADABS v2.13 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 6084 _diffrn_reflns_av_R_equivalents 0.0124 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 28.35 _reflns_number_total 2211 _reflns_number_gt 2081 _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^)+(0.0628P)^2^+0.0958P] 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 2211 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0366 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.1023 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 -0.04997(13) 0.55646(13) 0.21453(10) 0.01846(19) Uani 1 1 d . . . C2 C 0.01747(12) 0.67816(13) 0.07049(10) 0.01757(19) Uani 1 1 d . . . C3 C -0.07940(13) 0.81841(13) -0.06290(10) 0.0181(2) Uani 1 1 d . . . C4 C -0.27071(13) 0.89311(14) -0.10585(11) 0.0214(2) Uani 1 1 d . . . H4 H -0.3727 0.8489 -0.0407 0.026 Uiso 1 1 calc R . . C5 C -0.30405(15) 1.03589(15) -0.24944(12) 0.0248(2) Uani 1 1 d . . . H5 H -0.4305 1.0879 -0.2799 0.030 Uiso 1 1 calc R . . C6 C -0.15193(15) 1.10283(15) -0.34879(11) 0.0248(2) Uani 1 1 d . . . H6 H -0.1792 1.1979 -0.4440 0.030 Uiso 1 1 calc R . . C7 C 0.03971(15) 1.02973(14) -0.30771(11) 0.0232(2) Uani 1 1 d . . . H7 H 0.1419 1.0731 -0.3730 0.028 Uiso 1 1 calc R . . C8 C 0.06943(13) 0.88914(13) -0.16440(10) 0.0192(2) Uani 1 1 d . . . C9 C 0.21165(13) 0.67617(13) 0.04085(10) 0.01778(19) Uani 1 1 d . . . C10 C 0.35408(13) 0.55994(13) 0.14668(10) 0.01894(19) Uani 1 1 d . . . H10 H 0.4849 0.5610 0.1243 0.023 Uiso 1 1 calc R . . C11 C 0.28734(13) 0.44709(13) 0.28282(10) 0.01871(19) Uani 1 1 d . . . C12 C 0.40791(14) 0.31764(14) 0.41321(11) 0.0237(2) Uani 1 1 d . . . H12A H 0.5399 0.3303 0.3875 0.036 Uiso 1 1 calc R . . H12B H 0.4017 0.1819 0.4344 0.036 Uiso 1 1 calc R . . H12C H 0.3602 0.3570 0.5020 0.036 Uiso 1 1 calc R . . O1 O 0.09506(9) 0.44335(10) 0.31570(7) 0.01984(17) Uani 1 1 d . . . O2 O -0.21517(10) 0.54064(11) 0.25804(8) 0.02521(18) Uani 1 1 d . . . O3 O 0.24928(9) 0.80190(10) -0.10127(7) 0.02019(17) 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 0.0169(4) 0.0201(4) 0.0188(4) -0.0057(3) -0.0019(3) -0.0052(3) C2 0.0160(4) 0.0189(4) 0.0184(4) -0.0062(3) -0.0006(3) -0.0050(3) C3 0.0190(4) 0.0181(4) 0.0186(4) -0.0070(3) -0.0016(3) -0.0046(3) C4 0.0194(4) 0.0218(4) 0.0233(4) -0.0076(4) -0.0028(3) -0.0041(3) C5 0.0253(5) 0.0239(5) 0.0254(5) -0.0083(4) -0.0081(4) -0.0020(4) C6 0.0314(5) 0.0228(4) 0.0192(4) -0.0049(3) -0.0066(4) -0.0040(4) C7 0.0275(5) 0.0236(4) 0.0183(4) -0.0050(4) -0.0005(3) -0.0080(4) C8 0.0192(4) 0.0203(4) 0.0191(4) -0.0069(3) -0.0017(3) -0.0050(3) C9 0.0181(4) 0.0189(4) 0.0171(4) -0.0059(3) 0.0010(3) -0.0064(3) C10 0.0153(4) 0.0218(4) 0.0199(4) -0.0062(3) -0.0003(3) -0.0057(3) C11 0.0162(4) 0.0205(4) 0.0203(4) -0.0065(3) -0.0011(3) -0.0056(3) C12 0.0207(4) 0.0261(5) 0.0212(4) -0.0025(4) -0.0039(3) -0.0059(4) O1 0.0162(3) 0.0228(3) 0.0190(3) -0.0033(3) -0.0012(2) -0.0064(2) O2 0.0172(3) 0.0324(4) 0.0242(3) -0.0050(3) 0.0014(2) -0.0095(3) O3 0.0183(3) 0.0234(3) 0.0171(3) -0.0032(3) -0.0001(2) -0.0067(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 C1 O2 1.2142(11) . ? C1 O1 1.3962(10) . ? C1 C2 1.4295(12) . ? C2 C9 1.3736(12) . ? C2 C3 1.4426(12) . ? C3 C4 1.3966(12) . ? C3 C8 1.3984(12) . ? C4 C5 1.3935(13) . ? C4 H4 0.9300 . ? C5 C6 1.3986(15) . ? C5 H5 0.9300 . ? C6 C7 1.3934(14) . ? C6 H6 0.9300 . ? C7 C8 1.3827(13) . ? C7 H7 0.9300 . ? C8 O3 1.3935(11) . ? C9 O3 1.3646(10) . ? C9 C10 1.4130(12) . ? C10 C11 1.3529(12) . ? C10 H10 0.9300 . ? C11 O1 1.3702(11) . ? C11 C12 1.4844(12) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? 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 O2 C1 O1 117.28(8) . . ? O2 C1 C2 128.10(8) . . ? O1 C1 C2 114.62(8) . . ? C9 C2 C1 119.99(8) . . ? C9 C2 C3 106.81(8) . . ? C1 C2 C3 133.18(8) . . ? C4 C3 C8 119.15(8) . . ? C4 C3 C2 136.20(8) . . ? C8 C3 C2 104.64(8) . . ? C5 C4 C3 117.91(9) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? C4 C5 C6 121.59(9) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 121.20(9) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C8 C7 C6 116.26(9) . . ? C8 C7 H7 121.9 . . ? C6 C7 H7 121.9 . . ? C7 C8 O3 124.89(9) . . ? C7 C8 C3 123.89(9) . . ? O3 C8 C3 111.22(8) . . ? O3 C9 C2 111.95(8) . . ? O3 C9 C10 124.36(8) . . ? C2 C9 C10 123.68(8) . . ? C11 C10 C9 115.48(8) . . ? C11 C10 H10 122.3 . . ? C9 C10 H10 122.3 . . ? C10 C11 O1 122.46(8) . . ? C10 C11 C12 125.33(8) . . ? O1 C11 C12 112.20(8) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 O1 C1 123.76(7) . . ? C9 O3 C8 105.37(7) . . ? 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 O2 C1 C2 C9 -179.68(9) . . . . ? O1 C1 C2 C9 0.37(13) . . . . ? O2 C1 C2 C3 1.67(17) . . . . ? O1 C1 C2 C3 -178.28(9) . . . . ? C9 C2 C3 C4 -178.04(10) . . . . ? C1 C2 C3 C4 0.74(18) . . . . ? C9 C2 C3 C8 0.51(10) . . . . ? C1 C2 C3 C8 179.28(9) . . . . ? C8 C3 C4 C5 0.07(13) . . . . ? C2 C3 C4 C5 178.45(10) . . . . ? C3 C4 C5 C6 0.31(14) . . . . ? C4 C5 C6 C7 -0.28(15) . . . . ? C5 C6 C7 C8 -0.13(14) . . . . ? C6 C7 C8 O3 -178.46(8) . . . . ? C6 C7 C8 C3 0.53(14) . . . . ? C4 C3 C8 C7 -0.50(14) . . . . ? C2 C3 C8 C7 -179.35(9) . . . . ? C4 C3 C8 O3 178.61(7) . . . . ? C2 C3 C8 O3 -0.24(10) . . . . ? C1 C2 C9 O3 -179.59(7) . . . . ? C3 C2 C9 O3 -0.62(10) . . . . ? C1 C2 C9 C10 -0.65(14) . . . . ? C3 C2 C9 C10 178.31(8) . . . . ? O3 C9 C10 C11 178.88(8) . . . . ? C2 C9 C10 C11 0.07(14) . . . . ? C9 C10 C11 O1 0.79(13) . . . . ? C9 C10 C11 C12 -178.17(8) . . . . ? C10 C11 O1 C1 -1.10(14) . . . . ? C12 C11 O1 C1 177.97(8) . . . . ? O2 C1 O1 C11 -179.48(8) . . . . ? C2 C1 O1 C11 0.47(12) . . . . ? C2 C9 O3 C8 0.47(10) . . . . ? C10 C9 O3 C8 -178.46(8) . . . . ? C7 C8 O3 C9 178.98(9) . . . . ? C3 C8 O3 C9 -0.12(10) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.35 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.320 _refine_diff_density_min -0.233 _refine_diff_density_rms 0.047 # Attachment '- ijf0934.cif' data_ijf0934m _database_code_depnum_ccdc_archive 'CCDC 764709' #TrackingRef '- ijf0934.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H6 O3' _chemical_formula_sum 'C11 H6 O3' _chemical_formula_weight 186.16 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.1190(16) _cell_length_b 8.2091(12) _cell_length_c 18.856(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.787(2) _cell_angle_gamma 90.00 _cell_volume 1656.2(4) _cell_formula_units_Z 8 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 3453 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 28.30 _exptl_crystal_description Shard _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.800 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_process_details 'SADABS v2.10 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 8041 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0149 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2057 _reflns_number_gt 1765 _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^)+(0.0571P)^2^+0.9674P] 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 2057 _refine_ls_number_parameters 127 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0443 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 0.06541(10) 0.26444(14) 0.55902(6) 0.0214(2) Uani 1 1 d . . . C2 C 0.03945(11) 0.35284(15) 0.61759(7) 0.0255(3) Uani 1 1 d . . . H2 H -0.0209 0.4376 0.6096 0.031 Uiso 1 1 calc R . . C3 C 0.10630(11) 0.30814(15) 0.68524(7) 0.0275(3) Uani 1 1 d . . . H3 H 0.0930 0.3654 0.7262 0.033 Uiso 1 1 calc R . . C4 C 0.21995(10) 0.09436(15) 0.64273(6) 0.0240(2) Uani 1 1 d . . . C5 C 0.15101(10) 0.14039(13) 0.56995(6) 0.0201(2) Uani 1 1 d . . . C6 C 0.15265(10) 0.08235(13) 0.49811(6) 0.0201(2) Uani 1 1 d . . . C7 C 0.21758(10) -0.03716(14) 0.47109(6) 0.0237(2) Uani 1 1 d . . . H7 H 0.2771 -0.1050 0.5036 0.028 Uiso 1 1 calc R . . C8 C 0.19264(11) -0.05413(15) 0.39510(7) 0.0279(3) Uani 1 1 d . . . H8 H 0.2354 -0.1353 0.3755 0.033 Uiso 1 1 calc R . . C9 C 0.10598(11) 0.04595(16) 0.34717(6) 0.0289(3) Uani 1 1 d . . . H9 H 0.0923 0.0325 0.2955 0.035 Uiso 1 1 calc R . . C10 C 0.03901(11) 0.16500(15) 0.37288(6) 0.0270(3) Uani 1 1 d . . . H10 H -0.0209 0.2323 0.3404 0.032 Uiso 1 1 calc R . . C11 C 0.06518(10) 0.17927(13) 0.44869(6) 0.0216(2) Uani 1 1 d . . . O1 O 0.01080(7) 0.29158(10) 0.48602(4) 0.0240(2) Uani 1 1 d . . . O2 O 0.19246(8) 0.18498(11) 0.69877(4) 0.0280(2) Uani 1 1 d . . . O3 O 0.29777(8) -0.01200(12) 0.66034(5) 0.0337(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 0.0192(5) 0.0228(5) 0.0216(5) -0.0005(4) 0.0047(4) -0.0029(4) C2 0.0220(5) 0.0265(6) 0.0291(6) -0.0061(5) 0.0086(4) -0.0007(4) C3 0.0247(6) 0.0327(6) 0.0275(6) -0.0070(5) 0.0113(5) -0.0032(5) C4 0.0239(5) 0.0283(6) 0.0207(5) 0.0010(4) 0.0078(4) -0.0012(4) C5 0.0193(5) 0.0206(5) 0.0208(5) -0.0005(4) 0.0061(4) -0.0020(4) C6 0.0187(5) 0.0201(5) 0.0214(5) -0.0004(4) 0.0056(4) -0.0039(4) C7 0.0226(5) 0.0219(5) 0.0269(6) -0.0018(4) 0.0073(4) -0.0015(4) C8 0.0271(6) 0.0286(6) 0.0301(6) -0.0086(5) 0.0112(5) -0.0057(5) C9 0.0293(6) 0.0369(7) 0.0205(5) -0.0061(5) 0.0068(4) -0.0094(5) C10 0.0247(5) 0.0316(6) 0.0221(5) 0.0012(5) 0.0021(4) -0.0042(5) C11 0.0197(5) 0.0216(5) 0.0232(5) -0.0017(4) 0.0053(4) -0.0025(4) O1 0.0226(4) 0.0251(4) 0.0229(4) -0.0001(3) 0.0038(3) 0.0031(3) O2 0.0284(4) 0.0360(5) 0.0200(4) -0.0009(3) 0.0072(3) 0.0014(3) O3 0.0353(5) 0.0399(5) 0.0253(4) 0.0085(4) 0.0072(4) 0.0129(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 O1 1.3631(13) . ? C1 C5 1.3707(15) . ? C1 C2 1.4154(16) . ? C2 C3 1.3410(17) . ? C2 H2 0.9500 . ? C3 O2 1.3682(15) . ? C3 H3 0.9500 . ? C4 O3 1.2105(14) . ? C4 O2 1.3926(14) . ? C4 C5 1.4287(15) . ? C5 C6 1.4407(15) . ? C6 C7 1.3940(15) . ? C6 C11 1.3980(15) . ? C7 C8 1.3905(16) . ? C7 H7 0.9500 . ? C8 C9 1.3951(18) . ? C8 H8 0.9500 . ? C9 C10 1.3932(18) . ? C9 H9 0.9500 . ? C10 C11 1.3841(16) . ? C10 H10 0.9500 . ? C11 O1 1.3937(13) . ? 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 C5 111.94(9) . . ? O1 C1 C2 125.09(10) . . ? C5 C1 C2 122.97(10) . . ? C3 C2 C1 115.09(11) . . ? C3 C2 H2 122.5 . . ? C1 C2 H2 122.5 . . ? C2 C3 O2 123.95(11) . . ? C2 C3 H3 118.0 . . ? O2 C3 H3 118.0 . . ? O3 C4 O2 117.72(10) . . ? O3 C4 C5 127.66(11) . . ? O2 C4 C5 114.62(10) . . ? C1 C5 C4 120.67(10) . . ? C1 C5 C6 106.87(9) . . ? C4 C5 C6 132.45(10) . . ? C7 C6 C11 119.50(10) . . ? C7 C6 C5 135.78(10) . . ? C11 C6 C5 104.72(10) . . ? C8 C7 C6 117.99(11) . . ? C8 C7 H7 121.0 . . ? C6 C7 H7 121.0 . . ? C7 C8 C9 121.17(11) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 121.87(11) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C11 C10 C9 115.89(11) . . ? C11 C10 H10 122.1 . . ? C9 C10 H10 122.1 . . ? C10 C11 O1 125.41(10) . . ? C10 C11 C6 123.57(11) . . ? O1 C11 C6 111.01(9) . . ? C1 O1 C11 105.46(8) . . ? C3 O2 C4 122.70(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.46(10) . . . . ? C5 C1 C2 C3 0.93(17) . . . . ? C1 C2 C3 O2 -1.06(17) . . . . ? O1 C1 C5 C4 179.12(9) . . . . ? C2 C1 C5 C4 -0.34(17) . . . . ? O1 C1 C5 C6 0.24(12) . . . . ? C2 C1 C5 C6 -179.22(10) . . . . ? O3 C4 C5 C1 179.99(12) . . . . ? O2 C4 C5 C1 -0.16(15) . . . . ? O3 C4 C5 C6 -1.5(2) . . . . ? O2 C4 C5 C6 178.39(11) . . . . ? C1 C5 C6 C7 179.41(12) . . . . ? C4 C5 C6 C7 0.7(2) . . . . ? C1 C5 C6 C11 -0.07(12) . . . . ? C4 C5 C6 C11 -178.76(11) . . . . ? C11 C6 C7 C8 0.41(16) . . . . ? C5 C6 C7 C8 -179.00(12) . . . . ? C6 C7 C8 C9 0.45(17) . . . . ? C7 C8 C9 C10 -1.17(18) . . . . ? C8 C9 C10 C11 0.94(17) . . . . ? C9 C10 C11 O1 178.89(10) . . . . ? C9 C10 C11 C6 -0.06(17) . . . . ? C7 C6 C11 C10 -0.62(17) . . . . ? C5 C6 C11 C10 178.96(10) . . . . ? C7 C6 C11 O1 -179.70(9) . . . . ? C5 C6 C11 O1 -0.13(12) . . . . ? C5 C1 O1 C11 -0.31(12) . . . . ? C2 C1 O1 C11 179.14(10) . . . . ? C10 C11 O1 C1 -178.79(11) . . . . ? C6 C11 O1 C1 0.27(11) . . . . ? C2 C3 O2 C4 0.62(18) . . . . ? O3 C4 O2 C3 179.92(10) . . . . ? C5 C4 O2 C3 0.05(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.346 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.043 # Attachment '- ijf0936m.cif' data_ijf0936m _database_code_depnum_ccdc_archive 'CCDC 764710' #TrackingRef '- ijf0936m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C48 H39 I O3 P2 Pd' _chemical_formula_sum 'C48 H39 I O3 P2 Pd' _chemical_formula_weight 959.03 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' Pd Pd -0.9988 1.0072 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/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 10.2109(5) _cell_length_b 11.8937(6) _cell_length_c 34.1332(17) _cell_angle_alpha 90.00 _cell_angle_beta 93.0340(10) _cell_angle_gamma 90.00 _cell_volume 4139.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5062 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.86 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1920 _exptl_absorpt_coefficient_mu 1.313 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.790 _exptl_absorpt_correction_T_max 0.912 _exptl_absorpt_process_details 'SADABS v2.10 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 55989 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.30 _reflns_number_total 10290 _reflns_number_gt 8454 _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^)+(0.0329P)^2^+1.8115P] 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 10290 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0684 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.3820(3) -0.0788(2) 0.15900(8) 0.0219(6) Uani 1 1 d . . . C2 C 0.4906(3) -0.1501(3) 0.16278(9) 0.0298(7) Uani 1 1 d . . . H2 H 0.5057 -0.2037 0.1429 0.036 Uiso 1 1 calc R . . C3 C 0.5772(3) -0.1426(3) 0.19581(10) 0.0387(8) Uani 1 1 d . . . H3 H 0.6509 -0.1913 0.1983 0.046 Uiso 1 1 calc R . . C4 C 0.5566(3) -0.0658(3) 0.22452(9) 0.0388(8) Uani 1 1 d . . . H4 H 0.6154 -0.0617 0.2470 0.047 Uiso 1 1 calc R . . C5 C 0.4507(3) 0.0057(3) 0.22101(9) 0.0366(8) Uani 1 1 d . . . H5 H 0.4370 0.0591 0.2411 0.044 Uiso 1 1 calc R . . C6 C 0.3638(3) 0.0004(2) 0.18837(8) 0.0267(6) Uani 1 1 d . . . H6 H 0.2918 0.0509 0.1860 0.032 Uiso 1 1 calc R . . C7 C 0.3354(2) -0.1619(2) 0.07883(8) 0.0196(5) Uani 1 1 d . . . C8 C 0.3654(3) -0.2760(3) 0.08228(9) 0.0302(7) Uani 1 1 d . . . H8 H 0.3414 -0.3162 0.1049 0.036 Uiso 1 1 calc R . . C9 C 0.4296(3) -0.3313(3) 0.05321(10) 0.0364(8) Uani 1 1 d . . . H9 H 0.4519 -0.4085 0.0562 0.044 Uiso 1 1 calc R . . C10 C 0.4612(3) -0.2734(3) 0.01961(9) 0.0348(7) Uani 1 1 d . . . H10 H 0.5054 -0.3111 -0.0004 0.042 Uiso 1 1 calc R . . C11 C 0.4286(3) -0.1624(3) 0.01526(9) 0.0321(7) Uani 1 1 d . . . H11 H 0.4491 -0.1237 -0.0080 0.039 Uiso 1 1 calc R . . C12 C 0.3658(3) -0.1055(2) 0.04461(8) 0.0244(6) Uani 1 1 d . . . H12 H 0.3436 -0.0284 0.0413 0.029 Uiso 1 1 calc R . . C13 C 0.1372(3) -0.1821(2) 0.13521(8) 0.0193(5) Uani 1 1 d . . . C14 C 0.0527(3) -0.2373(2) 0.10815(8) 0.0231(6) Uani 1 1 d . . . H14 H 0.0663 -0.2318 0.0809 0.028 Uiso 1 1 calc R . . C15 C -0.0514(3) -0.3005(2) 0.12097(9) 0.0283(6) Uani 1 1 d . . . H15 H -0.1079 -0.3391 0.1025 0.034 Uiso 1 1 calc R . . C16 C -0.0729(3) -0.3073(2) 0.16066(9) 0.0314(7) Uani 1 1 d . . . H16 H -0.1450 -0.3493 0.1693 0.038 Uiso 1 1 calc R . . C17 C 0.0101(3) -0.2533(3) 0.18743(9) 0.0327(7) Uani 1 1 d . . . H17 H -0.0048 -0.2580 0.2146 0.039 Uiso 1 1 calc R . . C18 C 0.1158(3) -0.1917(2) 0.17494(8) 0.0268(6) Uani 1 1 d . . . H18 H 0.1738 -0.1559 0.1937 0.032 Uiso 1 1 calc R . . C19 C 0.1568(2) 0.3548(2) 0.05466(8) 0.0190(5) Uani 1 1 d . . . C20 C 0.1930(3) 0.2917(2) 0.02283(8) 0.0245(6) Uani 1 1 d . . . H20 H 0.2072 0.2131 0.0258 0.029 Uiso 1 1 calc R . . C21 C 0.2087(3) 0.3425(3) -0.01341(8) 0.0309(7) Uani 1 1 d . . . H21 H 0.2313 0.2983 -0.0352 0.037 Uiso 1 1 calc R . . C22 C 0.1914(3) 0.4566(3) -0.01752(9) 0.0333(7) Uani 1 1 d . . . H22 H 0.2026 0.4913 -0.0422 0.040 Uiso 1 1 calc R . . C23 C 0.1575(3) 0.5210(3) 0.01429(9) 0.0326(7) Uani 1 1 d . . . H23 H 0.1476 0.6001 0.0116 0.039 Uiso 1 1 calc R . . C24 C 0.1381(3) 0.4699(2) 0.05008(9) 0.0257(6) Uani 1 1 d . . . H24 H 0.1118 0.5139 0.0715 0.031 Uiso 1 1 calc R . . C25 C -0.0535(2) 0.3217(2) 0.10273(7) 0.0179(5) Uani 1 1 d . . . C26 C -0.1451(3) 0.2754(2) 0.07524(7) 0.0196(5) Uani 1 1 d . . . H26 H -0.1176 0.2221 0.0566 0.024 Uiso 1 1 calc R . . C27 C -0.2751(3) 0.3071(2) 0.07512(8) 0.0225(6) Uani 1 1 d . . . H27 H -0.3368 0.2755 0.0564 0.027 Uiso 1 1 calc R . . C28 C -0.3162(3) 0.3850(2) 0.10218(8) 0.0221(6) Uani 1 1 d . . . H28 H -0.4060 0.4062 0.1021 0.027 Uiso 1 1 calc R . . C29 C -0.2268(3) 0.4315(2) 0.12917(8) 0.0227(6) Uani 1 1 d . . . H29 H -0.2549 0.4849 0.1476 0.027 Uiso 1 1 calc R . . C30 C -0.0953(3) 0.4004(2) 0.12945(8) 0.0211(5) Uani 1 1 d . . . H30 H -0.0339 0.4331 0.1480 0.025 Uiso 1 1 calc R . . C31 C 0.1973(3) 0.3507(2) 0.14156(8) 0.0206(5) Uani 1 1 d . . . C32 C 0.1680(3) 0.3072(3) 0.17823(8) 0.0282(6) Uani 1 1 d . . . H32 H 0.1128 0.2432 0.1797 0.034 Uiso 1 1 calc R . . C33 C 0.2190(3) 0.3568(3) 0.21212(9) 0.0361(8) Uani 1 1 d . . . H33 H 0.1981 0.3273 0.2369 0.043 Uiso 1 1 calc R . . C34 C 0.2998(3) 0.4487(3) 0.21028(11) 0.0461(10) Uani 1 1 d . . . H34 H 0.3330 0.4835 0.2338 0.055 Uiso 1 1 calc R . . C35 C 0.3331(3) 0.4909(3) 0.17456(11) 0.0435(9) Uani 1 1 d . . . H35 H 0.3907 0.5533 0.1735 0.052 Uiso 1 1 calc R . . C36 C 0.2820(3) 0.4416(2) 0.14003(10) 0.0304(7) Uani 1 1 d . . . H36 H 0.3053 0.4703 0.1154 0.036 Uiso 1 1 calc R . . C37 C 0.0025(2) 0.0350(2) 0.09366(7) 0.0162(5) Uani 1 1 d . . . C38 C -0.0406(3) 0.0024(2) 0.05559(8) 0.0214(5) Uani 1 1 d . . . H38 H 0.0180 0.0079 0.0350 0.026 Uiso 1 1 calc R . . C39 C -0.1672(3) -0.0376(2) 0.04733(8) 0.0260(6) Uani 1 1 d . . . H39 H -0.1944 -0.0579 0.0212 0.031 Uiso 1 1 calc R . . C40 C -0.2529(3) -0.0477(2) 0.07700(9) 0.0280(6) Uani 1 1 d . . . H40 H -0.3393 -0.0750 0.0714 0.034 Uiso 1 1 calc R . . C41 C -0.2131(3) -0.0182(2) 0.11499(8) 0.0224(6) Uani 1 1 d . . . H41 H -0.2708 -0.0268 0.1357 0.027 Uiso 1 1 calc R . . C42 C -0.0875(2) 0.0240(2) 0.12234(7) 0.0172(5) Uani 1 1 d . . . C43 C -0.1241(3) 0.0893(2) 0.18761(7) 0.0187(5) Uani 1 1 d . . . C44 C -0.0989(3) 0.0597(2) 0.22547(8) 0.0222(6) Uani 1 1 d . . . H44 H -0.0288 0.0095 0.2320 0.027 Uiso 1 1 calc R . . C45 C -0.1754(3) 0.1024(2) 0.25568(8) 0.0219(6) Uani 1 1 d . . . C46 C -0.2999(3) 0.2070(2) 0.20545(7) 0.0199(5) Uani 1 1 d . . . C47 C -0.2286(3) 0.1649(2) 0.17688(8) 0.0200(5) Uani 1 1 d . . . H47 H -0.2472 0.1850 0.1502 0.024 Uiso 1 1 calc R . . C48 C -0.4106(3) 0.2880(2) 0.20071(8) 0.0231(6) Uani 1 1 d . . . H48A H -0.4333 0.2992 0.1727 0.035 Uiso 1 1 calc R . . H48B H -0.3847 0.3600 0.2127 0.035 Uiso 1 1 calc R . . H48C H -0.4868 0.2581 0.2136 0.035 Uiso 1 1 calc R . . I1 I 0.433542(16) 0.164731(15) 0.099160(5) 0.02224(5) Uani 1 1 d . . . O1 O -0.04088(17) 0.05013(16) 0.16074(5) 0.0202(4) Uani 1 1 d . . . O2 O -0.27437(18) 0.17760(15) 0.24398(5) 0.0211(4) Uani 1 1 d . . . O3 O -0.1654(2) 0.08010(17) 0.29051(5) 0.0299(5) Uani 1 1 d . . . P1 P 0.26014(6) -0.08521(6) 0.117887(19) 0.01661(13) Uani 1 1 d . . . P2 P 0.11891(6) 0.28088(6) 0.099237(19) 0.01644(13) Uani 1 1 d . . . Pd1 Pd 0.186637(18) 0.094232(16) 0.102199(5) 0.01450(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 C1 0.0193(13) 0.0241(14) 0.0221(13) 0.0066(11) 0.0008(10) -0.0046(11) C2 0.0234(15) 0.0336(17) 0.0324(16) 0.0093(13) 0.0023(12) -0.0011(13) C3 0.0257(16) 0.047(2) 0.0426(19) 0.0207(16) -0.0074(14) -0.0044(14) C4 0.0342(18) 0.052(2) 0.0290(16) 0.0175(15) -0.0107(13) -0.0202(16) C5 0.048(2) 0.0364(18) 0.0250(16) 0.0034(13) -0.0018(14) -0.0208(16) C6 0.0306(16) 0.0258(15) 0.0236(14) 0.0020(11) 0.0002(12) -0.0077(12) C7 0.0162(12) 0.0231(14) 0.0198(13) -0.0036(11) 0.0040(10) -0.0001(10) C8 0.0303(16) 0.0278(16) 0.0329(16) -0.0010(13) 0.0047(13) 0.0030(13) C9 0.0357(18) 0.0296(17) 0.0438(19) -0.0127(14) 0.0019(14) 0.0095(14) C10 0.0221(15) 0.050(2) 0.0329(17) -0.0193(15) 0.0043(12) 0.0050(14) C11 0.0256(15) 0.050(2) 0.0214(14) -0.0077(14) 0.0043(12) -0.0044(14) C12 0.0219(14) 0.0289(15) 0.0224(14) -0.0024(12) 0.0020(11) -0.0019(12) C13 0.0213(13) 0.0167(13) 0.0205(13) 0.0014(10) 0.0055(10) 0.0011(10) C14 0.0267(14) 0.0226(14) 0.0203(13) 0.0018(11) 0.0034(11) -0.0024(11) C15 0.0286(16) 0.0242(15) 0.0321(16) -0.0002(12) 0.0024(12) -0.0075(12) C16 0.0335(17) 0.0258(15) 0.0365(17) 0.0011(13) 0.0157(13) -0.0083(13) C17 0.0414(18) 0.0322(17) 0.0259(15) -0.0008(13) 0.0135(13) -0.0120(14) C18 0.0316(16) 0.0288(15) 0.0203(14) -0.0017(11) 0.0031(11) -0.0068(12) C19 0.0157(12) 0.0216(13) 0.0197(13) 0.0020(10) 0.0020(10) -0.0028(10) C20 0.0295(15) 0.0238(14) 0.0206(13) 0.0037(11) 0.0057(11) 0.0047(12) C21 0.0325(16) 0.0409(18) 0.0203(14) 0.0043(13) 0.0095(12) 0.0038(14) C22 0.0301(16) 0.0401(18) 0.0299(16) 0.0145(14) 0.0047(13) -0.0049(14) C23 0.0354(17) 0.0245(15) 0.0376(17) 0.0109(13) 0.0002(13) -0.0038(13) C24 0.0236(14) 0.0228(14) 0.0310(15) 0.0001(12) 0.0026(12) -0.0026(11) C25 0.0179(13) 0.0170(13) 0.0192(12) 0.0035(10) 0.0052(10) 0.0001(10) C26 0.0213(13) 0.0189(13) 0.0188(13) 0.0013(10) 0.0021(10) 0.0002(10) C27 0.0196(13) 0.0251(14) 0.0227(14) 0.0041(11) -0.0002(11) -0.0037(11) C28 0.0187(13) 0.0192(13) 0.0289(14) 0.0068(11) 0.0047(11) 0.0016(11) C29 0.0241(14) 0.0190(13) 0.0257(14) -0.0014(11) 0.0077(11) 0.0002(11) C30 0.0221(13) 0.0182(13) 0.0232(13) -0.0017(11) 0.0033(11) -0.0025(11) C31 0.0173(13) 0.0224(14) 0.0218(13) -0.0057(11) -0.0005(10) 0.0045(10) C32 0.0248(15) 0.0374(17) 0.0222(14) -0.0039(12) 0.0002(11) 0.0033(13) C33 0.0306(17) 0.054(2) 0.0229(15) -0.0093(14) -0.0035(12) 0.0147(15) C34 0.0318(18) 0.061(2) 0.044(2) -0.0282(18) -0.0175(15) 0.0125(17) C35 0.0305(18) 0.0343(18) 0.064(2) -0.0186(17) -0.0131(16) -0.0031(14) C36 0.0247(15) 0.0249(15) 0.0410(18) -0.0038(13) -0.0037(13) -0.0032(12) C37 0.0154(12) 0.0138(12) 0.0192(12) -0.0005(10) 0.0003(10) 0.0010(9) C38 0.0221(14) 0.0229(14) 0.0194(13) -0.0032(11) 0.0037(10) 0.0001(11) C39 0.0245(14) 0.0291(15) 0.0241(14) -0.0075(12) -0.0028(11) 0.0004(12) C40 0.0190(14) 0.0263(15) 0.0385(17) -0.0091(13) -0.0012(12) -0.0034(11) C41 0.0182(13) 0.0188(13) 0.0304(15) -0.0019(11) 0.0046(11) -0.0028(11) C42 0.0178(12) 0.0156(12) 0.0182(12) -0.0013(10) 0.0012(10) 0.0014(10) C43 0.0185(12) 0.0198(13) 0.0181(12) -0.0020(10) 0.0048(10) -0.0019(10) C44 0.0191(13) 0.0270(14) 0.0207(13) 0.0029(11) 0.0034(10) 0.0048(11) C45 0.0226(13) 0.0246(14) 0.0189(13) 0.0022(11) 0.0036(10) 0.0009(11) C46 0.0202(13) 0.0207(13) 0.0190(13) 0.0026(10) 0.0018(10) -0.0019(11) C47 0.0208(13) 0.0208(13) 0.0186(13) 0.0023(10) 0.0028(10) -0.0020(11) C48 0.0242(14) 0.0228(14) 0.0227(13) 0.0012(11) 0.0052(11) 0.0053(11) I1 0.01572(9) 0.02395(10) 0.02738(10) 0.00064(7) 0.00435(6) -0.00358(7) O1 0.0171(9) 0.0283(10) 0.0155(9) -0.0013(8) 0.0043(7) 0.0018(8) O2 0.0226(10) 0.0258(10) 0.0153(9) 0.0007(7) 0.0047(7) 0.0045(8) O3 0.0349(12) 0.0395(12) 0.0156(9) 0.0044(9) 0.0059(8) 0.0113(10) P1 0.0165(3) 0.0163(3) 0.0172(3) 0.0007(3) 0.0030(2) -0.0005(3) P2 0.0166(3) 0.0162(3) 0.0167(3) -0.0004(2) 0.0026(2) -0.0018(3) Pd1 0.01339(9) 0.01514(10) 0.01529(9) 0.00025(7) 0.00363(7) -0.00107(7) _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 C6 1.396(4) . ? C1 C2 1.396(4) . ? C1 P1 1.827(3) . ? C2 C3 1.398(4) . ? C2 H2 0.9500 . ? C3 C4 1.364(5) . ? C3 H3 0.9500 . ? C4 C5 1.376(5) . ? C4 H4 0.9500 . ? C5 C6 1.388(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.395(4) . ? C7 C12 1.396(4) . ? C7 P1 1.818(3) . ? C8 C9 1.384(4) . ? C8 H8 0.9500 . ? C9 C10 1.390(5) . ? C9 H9 0.9500 . ? C10 C11 1.368(5) . ? C10 H10 0.9500 . ? C11 C12 1.393(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C18 1.390(4) . ? C13 C14 1.395(4) . ? C13 P1 1.825(3) . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 C16 1.386(4) . ? C15 H15 0.9500 . ? C16 C17 1.373(4) . ? C16 H16 0.9500 . ? C17 C18 1.390(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.387(4) . ? C19 C24 1.390(4) . ? C19 P2 1.817(3) . ? C20 C21 1.393(4) . ? C20 H20 0.9500 . ? C21 C22 1.375(4) . ? C21 H21 0.9500 . ? C22 C23 1.388(4) . ? C22 H22 0.9500 . ? C23 C24 1.388(4) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.390(4) . ? C25 C26 1.402(4) . ? C25 P2 1.836(3) . ? C26 C27 1.380(4) . ? C26 H26 0.9500 . ? C27 C28 1.388(4) . ? C27 H27 0.9500 . ? C28 C29 1.379(4) . ? C28 H28 0.9500 . ? C29 C30 1.392(4) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C36 1.387(4) . ? C31 C32 1.401(4) . ? C31 P2 1.815(3) . ? C32 C33 1.376(4) . ? C32 H32 0.9500 . ? C33 C34 1.374(5) . ? C33 H33 0.9500 . ? C34 C35 1.377(5) . ? C34 H34 0.9500 . ? C35 C36 1.393(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 C42 1.384(3) . ? C37 C38 1.404(3) . ? C37 Pd1 2.014(2) . ? C38 C39 1.392(4) . ? C38 H38 0.9500 . ? C39 C40 1.379(4) . ? C39 H39 0.9500 . ? C40 C41 1.384(4) . ? C40 H40 0.9500 . ? C41 C42 1.387(4) . ? C41 H41 0.9500 . ? C42 O1 1.405(3) . ? C43 C44 1.350(4) . ? C43 O1 1.365(3) . ? C43 C47 1.428(4) . ? C44 C45 1.420(4) . ? C44 H44 0.9500 . ? C45 O3 1.217(3) . ? C45 O2 1.392(3) . ? C46 C47 1.344(4) . ? C46 O2 1.372(3) . ? C46 C48 1.488(4) . ? C47 H47 0.9500 . ? C48 H48A 0.9800 . ? C48 H48B 0.9800 . ? C48 H48C 0.9800 . ? I1 Pd1 2.6641(3) . ? P1 Pd1 2.3157(7) . ? P2 Pd1 2.3258(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 C6 C1 C2 118.6(3) . . ? C6 C1 P1 118.0(2) . . ? C2 C1 P1 123.5(2) . . ? C1 C2 C3 120.1(3) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.5(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C8 C7 C12 118.7(2) . . ? C8 C7 P1 121.7(2) . . ? C12 C7 P1 119.6(2) . . ? C9 C8 C7 120.8(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 119.7(3) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.6(3) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 120.0(3) . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? C18 C13 C14 118.9(2) . . ? C18 C13 P1 121.0(2) . . ? C14 C13 P1 119.6(2) . . ? C15 C14 C13 120.1(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 120.1(3) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C17 C16 C15 120.0(3) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C13 C18 C17 120.5(3) . . ? C13 C18 H18 119.7 . . ? C17 C18 H18 119.7 . . ? C20 C19 C24 119.1(2) . . ? C20 C19 P2 118.1(2) . . ? C24 C19 P2 122.5(2) . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C23 120.1(3) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C24 C23 C22 120.0(3) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C19 120.3(3) . . ? C23 C24 H24 119.8 . . ? C19 C24 H24 119.8 . . ? C30 C25 C26 119.1(2) . . ? C30 C25 P2 123.4(2) . . ? C26 C25 P2 117.42(19) . . ? C27 C26 C25 120.2(2) . . ? C27 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? C26 C27 C28 120.3(3) . . ? C26 C27 H27 119.8 . . ? C28 C27 H27 119.8 . . ? C29 C28 C27 119.9(3) . . ? C29 C28 H28 120.0 . . ? C27 C28 H28 120.0 . . ? C28 C29 C30 120.2(3) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C25 C30 C29 120.3(2) . . ? C25 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C36 C31 C32 119.0(3) . . ? C36 C31 P2 125.2(2) . . ? C32 C31 P2 115.8(2) . . ? C33 C32 C31 120.2(3) . . ? C33 C32 H32 119.9 . . ? C31 C32 H32 119.9 . . ? C34 C33 C32 120.3(3) . . ? C34 C33 H33 119.8 . . ? C32 C33 H33 119.8 . . ? C33 C34 C35 120.4(3) . . ? C33 C34 H34 119.8 . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 119.8(3) . . ? C34 C35 H35 120.1 . . ? C36 C35 H35 120.1 . . ? C31 C36 C35 120.2(3) . . ? C31 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C42 C37 C38 116.1(2) . . ? C42 C37 Pd1 125.49(19) . . ? C38 C37 Pd1 118.36(19) . . ? C39 C38 C37 121.6(2) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C40 C39 C38 120.0(3) . . ? C40 C39 H39 120.0 . . ? C38 C39 H39 120.0 . . ? C39 C40 C41 120.0(3) . . ? C39 C40 H40 120.0 . . ? C41 C40 H40 120.0 . . ? C40 C41 C42 119.0(3) . . ? C40 C41 H41 120.5 . . ? C42 C41 H41 120.5 . . ? C37 C42 C41 123.3(2) . . ? C37 C42 O1 115.7(2) . . ? C41 C42 O1 120.9(2) . . ? C44 C43 O1 117.4(2) . . ? C44 C43 C47 120.7(2) . . ? O1 C43 C47 121.7(2) . . ? C43 C44 C45 121.2(3) . . ? C43 C44 H44 119.4 . . ? C45 C44 H44 119.4 . . ? O3 C45 O2 116.3(2) . . ? O3 C45 C44 127.6(3) . . ? O2 C45 C44 116.1(2) . . ? C47 C46 O2 121.2(2) . . ? C47 C46 C48 126.9(2) . . ? O2 C46 C48 111.9(2) . . ? C46 C47 C43 118.3(2) . . ? C46 C47 H47 120.8 . . ? C43 C47 H47 120.8 . . ? C46 C48 H48A 109.5 . . ? C46 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C46 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? C43 O1 C42 120.7(2) . . ? C46 O2 C45 122.5(2) . . ? C7 P1 C13 104.21(12) . . ? C7 P1 C1 106.67(12) . . ? C13 P1 C1 103.27(12) . . ? C7 P1 Pd1 115.90(9) . . ? C13 P1 Pd1 115.89(9) . . ? C1 P1 Pd1 109.79(9) . . ? C31 P2 C19 109.91(13) . . ? C31 P2 C25 102.19(12) . . ? C19 P2 C25 100.00(12) . . ? C31 P2 Pd1 106.53(9) . . ? C19 P2 Pd1 114.99(9) . . ? C25 P2 Pd1 122.26(8) . . ? C37 Pd1 P1 89.98(7) . . ? C37 Pd1 P2 93.12(7) . . ? P1 Pd1 P2 169.03(2) . . ? C37 Pd1 I1 169.21(7) . . ? P1 Pd1 I1 90.189(18) . . ? P2 Pd1 I1 88.723(18) . . ? 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 C3 1.1(4) . . . . ? P1 C1 C2 C3 -177.8(2) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C3 C4 C5 C6 0.2(5) . . . . ? C4 C5 C6 C1 0.9(4) . . . . ? C2 C1 C6 C5 -1.6(4) . . . . ? P1 C1 C6 C5 177.4(2) . . . . ? C12 C7 C8 C9 3.0(4) . . . . ? P1 C7 C8 C9 -176.2(2) . . . . ? C7 C8 C9 C10 -1.9(5) . . . . ? C8 C9 C10 C11 -0.1(5) . . . . ? C9 C10 C11 C12 1.1(5) . . . . ? C10 C11 C12 C7 0.0(4) . . . . ? C8 C7 C12 C11 -2.0(4) . . . . ? P1 C7 C12 C11 177.2(2) . . . . ? C18 C13 C14 C15 0.2(4) . . . . ? P1 C13 C14 C15 -172.2(2) . . . . ? C13 C14 C15 C16 1.1(4) . . . . ? C14 C15 C16 C17 -1.2(5) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C14 C13 C18 C17 -1.4(4) . . . . ? P1 C13 C18 C17 170.9(2) . . . . ? C16 C17 C18 C13 1.3(5) . . . . ? C24 C19 C20 C21 -0.9(4) . . . . ? P2 C19 C20 C21 172.7(2) . . . . ? C19 C20 C21 C22 1.6(5) . . . . ? C20 C21 C22 C23 -0.4(5) . . . . ? C21 C22 C23 C24 -1.5(5) . . . . ? C22 C23 C24 C19 2.2(4) . . . . ? C20 C19 C24 C23 -1.1(4) . . . . ? P2 C19 C24 C23 -174.3(2) . . . . ? C30 C25 C26 C27 -0.6(4) . . . . ? P2 C25 C26 C27 -176.8(2) . . . . ? C25 C26 C27 C28 0.0(4) . . . . ? C26 C27 C28 C29 0.4(4) . . . . ? C27 C28 C29 C30 -0.2(4) . . . . ? C26 C25 C30 C29 0.8(4) . . . . ? P2 C25 C30 C29 176.8(2) . . . . ? C28 C29 C30 C25 -0.4(4) . . . . ? C36 C31 C32 C33 2.4(4) . . . . ? P2 C31 C32 C33 -177.7(2) . . . . ? C31 C32 C33 C34 -0.6(5) . . . . ? C32 C33 C34 C35 -1.4(5) . . . . ? C33 C34 C35 C36 1.5(5) . . . . ? C32 C31 C36 C35 -2.3(4) . . . . ? P2 C31 C36 C35 177.8(2) . . . . ? C34 C35 C36 C31 0.4(5) . . . . ? C42 C37 C38 C39 0.5(4) . . . . ? Pd1 C37 C38 C39 -179.0(2) . . . . ? C37 C38 C39 C40 -1.0(4) . . . . ? C38 C39 C40 C41 -0.1(4) . . . . ? C39 C40 C41 C42 1.6(4) . . . . ? C38 C37 C42 C41 1.1(4) . . . . ? Pd1 C37 C42 C41 -179.4(2) . . . . ? C38 C37 C42 O1 176.2(2) . . . . ? Pd1 C37 C42 O1 -4.3(3) . . . . ? C40 C41 C42 C37 -2.2(4) . . . . ? C40 C41 C42 O1 -177.0(2) . . . . ? O1 C43 C44 C45 176.0(2) . . . . ? C47 C43 C44 C45 0.2(4) . . . . ? C43 C44 C45 O3 177.7(3) . . . . ? C43 C44 C45 O2 -1.4(4) . . . . ? O2 C46 C47 C43 -0.6(4) . . . . ? C48 C46 C47 C43 178.8(3) . . . . ? C44 C43 C47 C46 0.9(4) . . . . ? O1 C43 C47 C46 -174.7(2) . . . . ? C44 C43 O1 C42 146.6(2) . . . . ? C47 C43 O1 C42 -37.6(3) . . . . ? C37 C42 O1 C43 151.7(2) . . . . ? C41 C42 O1 C43 -33.1(3) . . . . ? C47 C46 O2 C45 -0.7(4) . . . . ? C48 C46 O2 C45 179.7(2) . . . . ? O3 C45 O2 C46 -177.5(2) . . . . ? C44 C45 O2 C46 1.7(4) . . . . ? C8 C7 P1 C13 -41.4(3) . . . . ? C12 C7 P1 C13 139.4(2) . . . . ? C8 C7 P1 C1 67.4(3) . . . . ? C12 C7 P1 C1 -111.7(2) . . . . ? C8 C7 P1 Pd1 -170.0(2) . . . . ? C12 C7 P1 Pd1 10.8(2) . . . . ? C18 C13 P1 C7 140.6(2) . . . . ? C14 C13 P1 C7 -47.2(2) . . . . ? C18 C13 P1 C1 29.3(3) . . . . ? C14 C13 P1 C1 -158.5(2) . . . . ? C18 C13 P1 Pd1 -90.8(2) . . . . ? C14 C13 P1 Pd1 81.4(2) . . . . ? C6 C1 P1 C7 162.8(2) . . . . ? C2 C1 P1 C7 -18.3(3) . . . . ? C6 C1 P1 C13 -87.7(2) . . . . ? C2 C1 P1 C13 91.2(2) . . . . ? C6 C1 P1 Pd1 36.4(2) . . . . ? C2 C1 P1 Pd1 -144.6(2) . . . . ? C36 C31 P2 C19 -4.8(3) . . . . ? C32 C31 P2 C19 175.4(2) . . . . ? C36 C31 P2 C25 -110.3(2) . . . . ? C32 C31 P2 C25 69.9(2) . . . . ? C36 C31 P2 Pd1 120.4(2) . . . . ? C32 C31 P2 Pd1 -59.5(2) . . . . ? C20 C19 P2 C31 135.0(2) . . . . ? C24 C19 P2 C31 -51.7(3) . . . . ? C20 C19 P2 C25 -118.1(2) . . . . ? C24 C19 P2 C25 55.3(2) . . . . ? C20 C19 P2 Pd1 14.8(2) . . . . ? C24 C19 P2 Pd1 -171.88(19) . . . . ? C30 C25 P2 C31 7.9(2) . . . . ? C26 C25 P2 C31 -176.0(2) . . . . ? C30 C25 P2 C19 -105.1(2) . . . . ? C26 C25 P2 C19 70.9(2) . . . . ? C30 C25 P2 Pd1 126.6(2) . . . . ? C26 C25 P2 Pd1 -57.3(2) . . . . ? C42 C37 Pd1 P1 87.8(2) . . . . ? C38 C37 Pd1 P1 -92.7(2) . . . . ? C42 C37 Pd1 P2 -81.7(2) . . . . ? C38 C37 Pd1 P2 97.8(2) . . . . ? C42 C37 Pd1 I1 178.7(2) . . . . ? C38 C37 Pd1 I1 -1.8(5) . . . . ? C7 P1 Pd1 C37 99.34(12) . . . . ? C13 P1 Pd1 C37 -23.28(12) . . . . ? C1 P1 Pd1 C37 -139.75(12) . . . . ? C7 P1 Pd1 P2 -154.12(14) . . . . ? C13 P1 Pd1 P2 83.25(16) . . . . ? C1 P1 Pd1 P2 -33.22(17) . . . . ? C7 P1 Pd1 I1 -69.87(10) . . . . ? C13 P1 Pd1 I1 167.50(10) . . . . ? C1 P1 Pd1 I1 51.03(9) . . . . ? C31 P2 Pd1 C37 131.04(11) . . . . ? C19 P2 Pd1 C37 -106.94(12) . . . . ? C25 P2 Pd1 C37 14.44(12) . . . . ? C31 P2 Pd1 P1 24.80(17) . . . . ? C19 P2 Pd1 P1 146.82(14) . . . . ? C25 P2 Pd1 P1 -91.80(16) . . . . ? C31 P2 Pd1 I1 -59.60(9) . . . . ? C19 P2 Pd1 I1 62.43(9) . . . . ? C25 P2 Pd1 I1 -176.19(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.961 _refine_diff_density_min -0.341 _refine_diff_density_rms 0.099 # Attachment '- ijf1002m.cif' data_ijf1002m _database_code_depnum_ccdc_archive 'CCDC 764711' #TrackingRef '- ijf1002m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H24 O3 P, (F6 P1)0.98, (I)0.02' _chemical_formula_sum 'C30 H24 F5.86 I0.02 O3 P1.98' _chemical_formula_weight 608.43 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8107(8) _cell_length_b 13.2530(14) _cell_length_c 14.2579(15) _cell_angle_alpha 97.040(2) _cell_angle_beta 104.389(2) _cell_angle_gamma 104.932(2) _cell_volume 1353.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 4032 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.19 _exptl_crystal_description Shard _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.493 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.816 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'SADABS v2.10 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 13874 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 28.31 _reflns_number_total 6661 _reflns_number_gt 4951 _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. Anion was modelled as a disordered combination of PF6- and I- in a 98:2 ratio. The presence of I- is inferred from the large residual Q peak (1.5e) remaining after refinement of the PF6 group. Attempts to model the disorder as two PF6 anions were unsatisfactory. The close proximity of I1 to other atoms on the cation may be a consequence of unobserved cation disorder. As any disordered cation will occupy 2% of the electron density no attempt to model it was made. ; _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^)+(0.0686P)^2^+0.9271P] 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 6661 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1367 _refine_ls_wR_factor_gt 0.1227 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _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 0.0523(3) 0.10071(16) 0.78953(15) 0.0203(4) Uani 1 1 d . . . C2 C 0.0547(3) 0.01045(18) 0.83026(18) 0.0305(5) Uani 1 1 d . . . H2 H 0.1681 0.0046 0.8695 0.037 Uiso 1 1 calc R . . C3 C -0.1088(3) -0.07080(19) 0.8134(2) 0.0358(6) Uani 1 1 d . . . H3 H -0.1073 -0.1322 0.8412 0.043 Uiso 1 1 calc R . . C4 C -0.2742(3) -0.06260(19) 0.75609(17) 0.0298(5) Uani 1 1 d . . . H4 H -0.3856 -0.1190 0.7437 0.036 Uiso 1 1 calc R . . C5 C -0.2775(3) 0.02717(18) 0.71702(16) 0.0252(4) Uani 1 1 d . . . H5 H -0.3916 0.0328 0.6785 0.030 Uiso 1 1 calc R . . C6 C -0.1154(3) 0.10932(17) 0.73355(16) 0.0237(4) Uani 1 1 d . . . H6 H -0.1185 0.1713 0.7068 0.028 Uiso 1 1 calc R . . C7 C 0.4294(3) 0.19474(16) 0.91568(15) 0.0209(4) Uani 1 1 d . . . C8 C 0.3898(3) 0.21266(17) 1.00555(16) 0.0248(4) Uani 1 1 d . . . H8 H 0.2781 0.2276 1.0076 0.030 Uiso 1 1 calc R . . C9 C 0.5156(3) 0.20835(18) 1.09179(17) 0.0302(5) Uani 1 1 d . . . H9 H 0.4917 0.2227 1.1535 0.036 Uiso 1 1 calc R . . C10 C 0.6758(3) 0.18314(18) 1.08835(17) 0.0315(5) Uani 1 1 d . . . H10 H 0.7615 0.1805 1.1477 0.038 Uiso 1 1 calc R . . C11 C 0.7112(3) 0.16198(19) 0.99957(17) 0.0307(5) Uani 1 1 d . . . H11 H 0.8197 0.1429 0.9977 0.037 Uiso 1 1 calc R . . C12 C 0.5899(3) 0.16820(17) 0.91254(16) 0.0249(4) Uani 1 1 d . . . H12 H 0.6158 0.1545 0.8514 0.030 Uiso 1 1 calc R . . C13 C 0.2302(3) 0.33039(16) 0.80730(15) 0.0200(4) Uani 1 1 d . . . C14 C 0.2869(3) 0.40752(17) 0.89380(16) 0.0254(4) Uani 1 1 d . . . H14 H 0.3459 0.3931 0.9553 0.030 Uiso 1 1 calc R . . C15 C 0.2560(3) 0.50565(18) 0.88879(17) 0.0288(5) Uani 1 1 d . . . H15 H 0.2956 0.5589 0.9472 0.035 Uiso 1 1 calc R . . C16 C 0.1678(3) 0.52681(17) 0.79944(17) 0.0269(5) Uani 1 1 d . . . H16 H 0.1466 0.5940 0.7972 0.032 Uiso 1 1 calc R . . C17 C 0.1105(3) 0.45011(17) 0.71346(17) 0.0259(4) Uani 1 1 d . . . H17 H 0.0501 0.4647 0.6524 0.031 Uiso 1 1 calc R . . C18 C 0.1418(3) 0.35179(17) 0.71692(16) 0.0232(4) Uani 1 1 d . . . H18 H 0.1034 0.2992 0.6581 0.028 Uiso 1 1 calc R . . C19 C 0.3456(3) 0.17393(16) 0.69841(15) 0.0198(4) Uani 1 1 d . . . C20 C 0.2496(3) 0.08545(17) 0.62244(15) 0.0223(4) Uani 1 1 d . . . H20 H 0.1437 0.0345 0.6277 0.027 Uiso 1 1 calc R . . C21 C 0.3090(3) 0.07189(17) 0.53906(16) 0.0243(4) Uani 1 1 d . . . H21 H 0.2433 0.0116 0.4873 0.029 Uiso 1 1 calc R . . C22 C 0.4641(3) 0.14600(17) 0.53097(16) 0.0250(4) Uani 1 1 d . . . H22 H 0.5024 0.1367 0.4731 0.030 Uiso 1 1 calc R . . C23 C 0.5640(3) 0.23384(17) 0.60689(16) 0.0235(4) Uani 1 1 d . . . H23 H 0.6718 0.2837 0.6022 0.028 Uiso 1 1 calc R . . C24 C 0.5027(3) 0.24678(16) 0.68893(15) 0.0202(4) Uani 1 1 d . . . O3 O 0.6043(2) 0.32800(11) 0.77136(11) 0.0239(3) Uani 1 1 d . . . C26 C 0.6361(3) 0.43297(16) 0.76364(16) 0.0230(4) Uani 1 1 d . . . C27 C 0.7564(3) 0.50541(18) 0.84326(17) 0.0289(5) Uani 1 1 d . . . H27 H 0.8191 0.4824 0.8987 0.035 Uiso 1 1 calc R . . C28 C 0.7888(3) 0.61676(19) 0.8437(2) 0.0347(6) Uani 1 1 d . . . C29 C 0.5735(3) 0.56976(19) 0.68049(19) 0.0317(5) Uani 1 1 d . . . C30 C 0.5428(3) 0.46489(17) 0.67846(17) 0.0260(4) Uani 1 1 d . . . H30 H 0.4615 0.4136 0.6220 0.031 Uiso 1 1 calc R . . C31 C 0.4848(4) 0.6192(2) 0.6014(2) 0.0448(7) Uani 1 1 d . . . H31A H 0.4033 0.5633 0.5448 0.067 Uiso 1 1 calc R . . H31B H 0.5808 0.6669 0.5806 0.067 Uiso 1 1 calc R . . H31C H 0.4120 0.6602 0.6267 0.067 Uiso 1 1 calc R . . O1 O 0.8910(3) 0.69005(14) 0.90992(15) 0.0460(5) Uani 1 1 d . . . O2 O 0.6908(2) 0.64403(13) 0.76047(14) 0.0360(4) Uani 1 1 d . . . P1 P 0.26664(7) 0.20120(4) 0.80470(4) 0.01861(13) Uani 1 1 d . . . F1 F -0.1580(2) 0.69413(13) 0.50830(11) 0.0430(4) Uani 0.9764(11) 1 d P A 1 F2 F 0.1157(3) 0.6652(2) 0.51950(17) 0.0869(9) Uani 0.9764(11) 1 d P A 1 F3 F 0.0142(3) 0.67741(17) 0.65588(14) 0.0705(6) Uani 0.9764(11) 1 d P A 1 F4 F 0.2585(2) 0.80812(17) 0.64983(15) 0.0658(6) Uani 0.9764(11) 1 d P A 1 F5 F -0.0146(3) 0.84240(15) 0.62873(15) 0.0598(5) Uani 0.9764(11) 1 d P A 1 F6 F 0.0903(3) 0.8206(2) 0.49821(16) 0.0797(8) Uani 0.9764(11) 1 d P A 1 P2 P 0.04963(8) 0.75056(5) 0.58014(5) 0.02986(17) Uani 0.9764(11) 1 d P A 1 I1 I 0.1426(13) 0.7520(8) 0.5048(7) 0.049(3) Uani 0.0236(11) 1 d P A 2 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 0.0193(9) 0.0191(9) 0.0215(10) 0.0028(8) 0.0049(8) 0.0055(7) C2 0.0228(10) 0.0270(11) 0.0384(13) 0.0117(10) 0.0022(9) 0.0062(9) C3 0.0317(12) 0.0269(12) 0.0434(14) 0.0152(11) 0.0035(11) 0.0029(10) C4 0.0228(10) 0.0284(12) 0.0326(12) 0.0069(10) 0.0058(9) 0.0003(9) C5 0.0196(10) 0.0299(11) 0.0254(11) 0.0035(9) 0.0054(8) 0.0081(8) C6 0.0238(10) 0.0233(10) 0.0251(11) 0.0061(8) 0.0055(8) 0.0097(8) C7 0.0200(9) 0.0184(10) 0.0221(10) 0.0031(8) 0.0027(8) 0.0057(8) C8 0.0270(10) 0.0239(11) 0.0244(11) 0.0069(8) 0.0077(9) 0.0083(8) C9 0.0406(13) 0.0271(11) 0.0214(11) 0.0068(9) 0.0080(10) 0.0075(10) C10 0.0337(12) 0.0279(12) 0.0249(11) 0.0073(9) -0.0035(9) 0.0066(10) C11 0.0235(10) 0.0322(12) 0.0325(12) 0.0063(10) -0.0012(9) 0.0111(9) C12 0.0225(10) 0.0262(11) 0.0244(11) 0.0035(9) 0.0034(8) 0.0086(8) C13 0.0174(9) 0.0182(9) 0.0245(10) 0.0051(8) 0.0055(8) 0.0058(7) C14 0.0258(10) 0.0241(11) 0.0251(11) 0.0044(9) 0.0044(9) 0.0087(9) C15 0.0319(12) 0.0225(11) 0.0303(12) -0.0002(9) 0.0080(9) 0.0087(9) C16 0.0250(10) 0.0208(10) 0.0366(12) 0.0074(9) 0.0080(9) 0.0098(8) C17 0.0230(10) 0.0262(11) 0.0289(11) 0.0098(9) 0.0050(9) 0.0086(8) C18 0.0220(10) 0.0225(10) 0.0229(10) 0.0037(8) 0.0046(8) 0.0051(8) C19 0.0205(9) 0.0205(10) 0.0201(10) 0.0058(8) 0.0045(8) 0.0096(8) C20 0.0193(9) 0.0213(10) 0.0246(10) 0.0048(8) 0.0026(8) 0.0065(8) C21 0.0243(10) 0.0223(10) 0.0240(10) 0.0012(8) 0.0026(8) 0.0087(8) C22 0.0281(11) 0.0272(11) 0.0230(11) 0.0072(9) 0.0077(9) 0.0127(9) C23 0.0223(10) 0.0228(10) 0.0262(11) 0.0072(8) 0.0067(8) 0.0077(8) C24 0.0198(9) 0.0172(9) 0.0205(10) 0.0025(8) 0.0014(7) 0.0056(7) O3 0.0244(7) 0.0203(7) 0.0216(7) 0.0023(6) 0.0029(6) 0.0021(6) C26 0.0201(9) 0.0198(10) 0.0287(11) 0.0012(8) 0.0122(8) 0.0022(8) C27 0.0245(11) 0.0281(11) 0.0301(12) -0.0014(9) 0.0106(9) 0.0017(9) C28 0.0277(11) 0.0270(12) 0.0465(15) -0.0065(11) 0.0211(11) -0.0002(9) C29 0.0313(12) 0.0271(12) 0.0424(14) 0.0076(10) 0.0203(11) 0.0087(9) C30 0.0252(10) 0.0222(10) 0.0309(12) 0.0042(9) 0.0107(9) 0.0054(8) C31 0.0510(16) 0.0340(14) 0.0602(18) 0.0212(13) 0.0221(14) 0.0199(12) O1 0.0358(10) 0.0306(10) 0.0579(13) -0.0157(9) 0.0165(9) -0.0047(8) O2 0.0366(9) 0.0215(8) 0.0499(11) 0.0023(7) 0.0196(8) 0.0045(7) P1 0.0170(2) 0.0183(2) 0.0197(3) 0.00403(19) 0.00338(19) 0.00567(19) F1 0.0262(7) 0.0545(10) 0.0378(8) 0.0023(7) 0.0058(6) 0.0009(7) F2 0.0690(14) 0.107(2) 0.0727(15) -0.0302(14) -0.0037(12) 0.0512(14) F3 0.0906(16) 0.0687(13) 0.0502(12) 0.0337(10) 0.0101(11) 0.0203(12) F4 0.0293(9) 0.0838(14) 0.0596(12) -0.0121(10) -0.0144(8) 0.0135(9) F5 0.0545(11) 0.0508(11) 0.0713(13) -0.0107(9) 0.0187(10) 0.0213(9) F6 0.0808(16) 0.0768(17) 0.0569(13) 0.0141(12) 0.0165(11) -0.0148(14) P2 0.0258(3) 0.0321(3) 0.0279(3) 0.0019(3) 0.0023(2) 0.0096(2) I1 0.058(5) 0.037(6) 0.065(6) 0.015(4) 0.028(4) 0.024(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 1.395(3) . ? C1 C6 1.395(3) . ? C1 P1 1.795(2) . ? C2 C3 1.387(3) . ? C2 H2 0.9500 . ? C3 C4 1.385(3) . ? C3 H3 0.9500 . ? C4 C5 1.378(3) . ? C4 H4 0.9500 . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.396(3) . ? C7 C8 1.398(3) . ? C7 P1 1.794(2) . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 C10 1.387(3) . ? C9 H9 0.9500 . ? C10 C11 1.373(3) . ? C10 H10 0.9500 . ? C11 C12 1.388(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.396(3) . ? C13 C18 1.402(3) . ? C13 P1 1.804(2) . ? C14 C15 1.390(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 C17 1.387(3) . ? C16 H16 0.9500 . ? C17 C18 1.391(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.394(3) . ? C19 C24 1.400(3) . ? C19 P1 1.803(2) . ? C20 C21 1.388(3) . ? C20 H20 0.9500 . ? C21 C22 1.389(3) . ? C21 H21 0.9500 . ? C22 C23 1.393(3) . ? C22 H22 0.9500 . ? C23 C24 1.378(3) . ? C23 H23 0.9500 . ? C24 O3 1.399(2) . ? O3 C26 1.372(3) . ? C26 C27 1.353(3) . ? C26 C30 1.425(3) . ? C27 C28 1.430(3) . ? C27 H27 0.9500 . ? C28 O1 1.213(3) . ? C28 O2 1.387(3) . ? C29 C30 1.344(3) . ? C29 O2 1.360(3) . ? C29 C31 1.486(4) . ? C30 H30 0.9500 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? F1 P2 1.6126(15) . ? F2 P2 1.605(2) . ? F3 P2 1.5651(19) . ? F4 P2 1.6117(17) . ? F5 P2 1.5794(18) . ? F6 P2 1.620(2) . ? 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 119.61(19) . . ? C2 C1 P1 119.49(16) . . ? C6 C1 P1 120.83(16) . . ? C3 C2 C1 119.8(2) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.1(2) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 119.8(2) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? C12 C7 C8 120.12(19) . . ? C12 C7 P1 120.88(16) . . ? C8 C7 P1 118.96(16) . . ? C9 C8 C7 119.3(2) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C10 C9 C8 120.3(2) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C11 C10 C9 120.3(2) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C11 C12 C7 119.4(2) . . ? C11 C12 H12 120.3 . . ? C7 C12 H12 120.3 . . ? C14 C13 C18 120.18(19) . . ? C14 C13 P1 122.93(16) . . ? C18 C13 P1 116.89(16) . . ? C15 C14 C13 119.1(2) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C15 C14 120.8(2) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C17 C16 C15 120.2(2) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.8(2) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C13 119.9(2) . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? C20 C19 C24 118.60(19) . . ? C20 C19 P1 122.16(16) . . ? C24 C19 P1 119.14(15) . . ? C21 C20 C19 119.94(19) . . ? C21 C20 H20 120.0 . . ? C19 C20 H20 120.0 . . ? C20 C21 C22 120.3(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C21 C22 C23 120.6(2) . . ? C21 C22 H22 119.7 . . ? C23 C22 H22 119.7 . . ? C24 C23 C22 118.5(2) . . ? C24 C23 H23 120.8 . . ? C22 C23 H23 120.8 . . ? C23 C24 O3 121.50(18) . . ? C23 C24 C19 122.05(19) . . ? O3 C24 C19 116.18(18) . . ? C26 O3 C24 120.54(16) . . ? C27 C26 O3 116.2(2) . . ? C27 C26 C30 121.5(2) . . ? O3 C26 C30 122.26(19) . . ? C26 C27 C28 119.9(2) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? O1 C28 O2 116.4(2) . . ? O1 C28 C27 126.9(3) . . ? O2 C28 C27 116.6(2) . . ? C30 C29 O2 121.7(2) . . ? C30 C29 C31 126.3(2) . . ? O2 C29 C31 112.0(2) . . ? C29 C30 C26 117.9(2) . . ? C29 C30 H30 121.0 . . ? C26 C30 H30 121.0 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 O2 C28 122.42(19) . . ? C7 P1 C1 107.61(10) . . ? C7 P1 C19 111.03(9) . . ? C1 P1 C19 108.39(9) . . ? C7 P1 C13 112.69(10) . . ? C1 P1 C13 110.22(9) . . ? C19 P1 C13 106.83(9) . . ? F3 P2 F5 95.29(12) . . ? F3 P2 F2 91.88(15) . . ? F5 P2 F2 172.74(15) . . ? F3 P2 F4 90.19(12) . . ? F5 P2 F4 89.67(11) . . ? F2 P2 F4 91.42(11) . . ? F3 P2 F1 91.10(11) . . ? F5 P2 F1 90.58(10) . . ? F2 P2 F1 88.17(10) . . ? F4 P2 F1 178.65(11) . . ? F3 P2 F6 176.42(15) . . ? F5 P2 F6 88.28(14) . . ? F2 P2 F6 84.54(17) . . ? F4 P2 F6 89.91(12) . . ? F1 P2 F6 88.78(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 C6 C1 C2 C3 1.1(4) . . . . ? P1 C1 C2 C3 -175.8(2) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C2 C3 C4 C5 -1.2(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C4 C5 C6 C1 0.4(3) . . . . ? C2 C1 C6 C5 -1.4(3) . . . . ? P1 C1 C6 C5 175.43(16) . . . . ? C12 C7 C8 C9 2.8(3) . . . . ? P1 C7 C8 C9 -179.67(16) . . . . ? C7 C8 C9 C10 -2.1(3) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 1.7(4) . . . . ? C10 C11 C12 C7 -0.9(3) . . . . ? C8 C7 C12 C11 -1.3(3) . . . . ? P1 C7 C12 C11 -178.81(17) . . . . ? C18 C13 C14 C15 -0.5(3) . . . . ? P1 C13 C14 C15 178.95(17) . . . . ? C13 C14 C15 C16 0.8(3) . . . . ? C14 C15 C16 C17 -0.5(3) . . . . ? C15 C16 C17 C18 0.0(3) . . . . ? C16 C17 C18 C13 0.3(3) . . . . ? C14 C13 C18 C17 0.0(3) . . . . ? P1 C13 C18 C17 -179.55(16) . . . . ? C24 C19 C20 C21 -0.9(3) . . . . ? P1 C19 C20 C21 175.60(16) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 1.1(3) . . . . ? C21 C22 C23 C24 -1.6(3) . . . . ? C22 C23 C24 O3 174.60(18) . . . . ? C22 C23 C24 C19 0.8(3) . . . . ? C20 C19 C24 C23 0.4(3) . . . . ? P1 C19 C24 C23 -176.20(16) . . . . ? C20 C19 C24 O3 -173.69(17) . . . . ? P1 C19 C24 O3 9.7(2) . . . . ? C23 C24 O3 C26 62.9(3) . . . . ? C19 C24 O3 C26 -123.0(2) . . . . ? C24 O3 C26 C27 -171.26(18) . . . . ? C24 O3 C26 C30 11.2(3) . . . . ? O3 C26 C27 C28 -176.21(19) . . . . ? C30 C26 C27 C28 1.4(3) . . . . ? C26 C27 C28 O1 179.4(2) . . . . ? C26 C27 C28 O2 0.6(3) . . . . ? O2 C29 C30 C26 0.6(3) . . . . ? C31 C29 C30 C26 -177.5(2) . . . . ? C27 C26 C30 C29 -2.0(3) . . . . ? O3 C26 C30 C29 175.45(19) . . . . ? C30 C29 O2 C28 1.4(3) . . . . ? C31 C29 O2 C28 179.7(2) . . . . ? O1 C28 O2 C29 179.1(2) . . . . ? C27 C28 O2 C29 -2.0(3) . . . . ? C12 C7 P1 C1 116.67(18) . . . . ? C8 C7 P1 C1 -60.84(19) . . . . ? C12 C7 P1 C19 -1.8(2) . . . . ? C8 C7 P1 C19 -179.31(16) . . . . ? C12 C7 P1 C13 -121.60(17) . . . . ? C8 C7 P1 C13 60.89(19) . . . . ? C2 C1 P1 C7 -26.5(2) . . . . ? C6 C1 P1 C7 156.64(17) . . . . ? C2 C1 P1 C19 93.65(19) . . . . ? C6 C1 P1 C19 -83.21(19) . . . . ? C2 C1 P1 C13 -149.75(18) . . . . ? C6 C1 P1 C13 33.4(2) . . . . ? C20 C19 P1 C7 116.07(17) . . . . ? C24 C19 P1 C7 -67.46(18) . . . . ? C20 C19 P1 C1 -1.93(19) . . . . ? C24 C19 P1 C1 174.54(15) . . . . ? C20 C19 P1 C13 -120.69(17) . . . . ? C24 C19 P1 C13 55.78(18) . . . . ? C14 C13 P1 C7 -14.3(2) . . . . ? C18 C13 P1 C7 165.16(15) . . . . ? C14 C13 P1 C1 105.90(18) . . . . ? C18 C13 P1 C1 -74.60(18) . . . . ? C14 C13 P1 C19 -136.54(18) . . . . ? C18 C13 P1 C19 42.96(18) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.665 _refine_diff_density_min -0.691 _refine_diff_density_rms 0.067 # Attachment '- ijf0930.cif' data_ijf0930 _database_code_depnum_ccdc_archive 'CCDC 773153' #TrackingRef '- ijf0930.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 F O3' _chemical_formula_sum 'C12 H7 F O3' _chemical_formula_weight 218.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7437(3) _cell_length_b 6.3700(7) _cell_length_c 19.0219(19) _cell_angle_alpha 91.665(9) _cell_angle_beta 90.858(7) _cell_angle_gamma 93.699(8) _cell_volume 452.42(8) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3693 _cell_measurement_theta_min 4.6369 _cell_measurement_theta_max 70.6948 _exptl_crystal_description Block _exptl_crystal_colour 'Pale red' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 1.102 _exptl_absorpt_correction_T_min 0.76940 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Onyx' _diffrn_detector_area_resol_mean 8.2707 _diffrn_reflns_number 7806 _diffrn_reflns_av_R_equivalents 0.0390 _diffrn_reflns_av_sigmaI/netI 0.0357 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.65 _diffrn_reflns_theta_max 70.79 _reflns_number_total 1688 _reflns_number_gt 1415 _reflns_threshold_expression >2sigma(I) _diffrn_measurement_method '\w scans' _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0772P)^2^+0.2340P] 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 1688 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1316 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.0908(5) 0.4231(3) 0.26954(11) 0.0240(4) Uani 1 1 d . . . C2 C 0.0447(5) 0.2794(3) 0.32406(11) 0.0257(5) Uani 1 1 d . . . H2 H -0.0714 0.1469 0.3168 0.031 Uiso 1 1 calc R . . C3 C 0.1798(5) 0.3465(3) 0.38752(11) 0.0259(5) Uani 1 1 d . . . C4 C 0.1623(6) 0.2248(3) 0.45275(11) 0.0314(5) Uani 1 1 d . . . H4A H 0.0332 0.0916 0.4433 0.047 Uiso 1 1 calc R . . H4B H 0.0419 0.3020 0.4883 0.047 Uiso 1 1 calc R . . H4C H 0.4006 0.2020 0.4689 0.047 Uiso 1 1 calc R . . C5 C 0.4099(5) 0.6887(3) 0.34526(11) 0.0245(4) Uani 1 1 d . . . C6 C 0.2627(5) 0.6205(3) 0.27808(11) 0.0237(4) Uani 1 1 d . . . C7 C 0.2505(5) 0.7172(3) 0.21064(10) 0.0226(4) Uani 1 1 d . . . C8 C 0.3670(5) 0.9120(3) 0.18337(11) 0.0249(4) Uani 1 1 d . . . H8 H 0.4877 1.0172 0.2111 0.030 Uiso 1 1 calc R . . C9 C 0.2926(5) 0.9379(3) 0.11360(11) 0.0272(5) Uani 1 1 d . . . C10 C 0.1145(5) 0.7860(3) 0.06950(12) 0.0285(5) Uani 1 1 d . . . H10 H 0.0746 0.8132 0.0224 0.034 Uiso 1 1 calc R . . C11 C -0.0034(5) 0.5935(3) 0.09627(11) 0.0278(5) Uani 1 1 d . . . H11 H -0.1253 0.4893 0.0683 0.033 Uiso 1 1 calc R . . C12 C 0.0698(5) 0.5655(3) 0.16604(11) 0.0243(4) Uani 1 1 d . . . F1 F 0.4031(3) 1.12463(19) 0.08454(7) 0.0359(4) Uani 1 1 d . . . O1 O -0.0287(3) 0.3839(2) 0.20248(7) 0.0253(4) Uani 1 1 d . . . O2 O 0.5760(4) 0.8535(2) 0.36164(8) 0.0313(4) Uani 1 1 d . . . O3 O 0.3521(3) 0.5429(2) 0.39809(7) 0.0263(4) 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 0.0205(8) 0.0270(10) 0.0238(11) -0.0047(8) 0.0016(7) -0.0015(7) C2 0.0238(9) 0.0257(10) 0.0267(11) -0.0025(8) 0.0023(8) -0.0032(7) C3 0.0217(9) 0.0256(10) 0.0298(12) -0.0020(8) 0.0032(8) -0.0033(7) C4 0.0320(10) 0.0340(11) 0.0275(12) 0.0011(9) 0.0016(9) -0.0051(8) C5 0.0218(9) 0.0268(10) 0.0243(11) -0.0020(8) 0.0037(8) -0.0022(7) C6 0.0192(8) 0.0260(10) 0.0251(11) -0.0032(8) 0.0015(7) -0.0018(7) C7 0.0179(8) 0.0263(10) 0.0233(11) -0.0034(8) 0.0023(7) 0.0004(7) C8 0.0229(9) 0.0257(10) 0.0254(11) -0.0036(8) 0.0029(8) -0.0017(7) C9 0.0264(9) 0.0258(10) 0.0292(12) 0.0017(8) 0.0045(8) -0.0001(8) C10 0.0286(10) 0.0335(11) 0.0234(11) -0.0019(8) 0.0008(8) 0.0035(8) C11 0.0274(9) 0.0295(10) 0.0259(12) -0.0064(8) -0.0003(8) 0.0008(8) C12 0.0221(9) 0.0250(9) 0.0254(11) -0.0026(8) 0.0033(7) -0.0013(7) F1 0.0449(7) 0.0303(7) 0.0320(7) 0.0050(5) 0.0030(6) -0.0046(5) O1 0.0262(7) 0.0258(7) 0.0228(8) -0.0032(6) -0.0006(6) -0.0048(5) O2 0.0334(7) 0.0300(7) 0.0284(8) -0.0044(6) -0.0010(6) -0.0100(6) O3 0.0258(7) 0.0269(7) 0.0251(8) -0.0029(6) 0.0009(5) -0.0059(5) _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 1.356(2) . ? C1 C6 1.379(3) . ? C1 C2 1.408(3) . ? C2 C3 1.349(3) . ? C2 H2 0.9300 . ? C3 O3 1.378(2) . ? C3 C4 1.482(3) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 O2 1.215(2) . ? C5 O3 1.398(2) . ? C5 C6 1.429(3) . ? C6 C7 1.441(3) . ? C7 C12 1.401(3) . ? C7 C8 1.405(3) . ? C8 C9 1.369(3) . ? C8 H8 0.9300 . ? C9 F1 1.369(2) . ? C9 C10 1.392(3) . ? C10 C11 1.389(3) . ? C10 H10 0.9300 . ? C11 C12 1.370(3) . ? C11 H11 0.9300 . ? C12 O1 1.398(2) . ? 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 C6 112.00(18) . . ? O1 C1 C2 124.06(17) . . ? C6 C1 C2 123.94(19) . . ? C3 C2 C1 115.66(18) . . ? C3 C2 H2 122.2 . . ? C1 C2 H2 122.2 . . ? C2 C3 O3 122.01(19) . . ? C2 C3 C4 125.61(19) . . ? O3 C3 C4 112.38(18) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 O3 117.17(19) . . ? O2 C5 C6 128.67(19) . . ? O3 C5 C6 114.16(16) . . ? C1 C6 C5 119.95(19) . . ? C1 C6 C7 106.72(18) . . ? C5 C6 C7 133.33(18) . . ? C12 C7 C8 119.08(19) . . ? C12 C7 C6 104.74(16) . . ? C8 C7 C6 136.18(19) . . ? C9 C8 C7 116.11(18) . . ? C9 C8 H8 121.9 . . ? C7 C8 H8 121.9 . . ? F1 C9 C8 118.22(18) . . ? F1 C9 C10 117.27(19) . . ? C8 C9 C10 124.50(19) . . ? C11 C10 C9 119.7(2) . . ? C11 C10 H10 120.2 . . ? C9 C10 H10 120.2 . . ? C12 C11 C10 116.42(19) . . ? C12 C11 H11 121.8 . . ? C10 C11 H11 121.8 . . ? C11 C12 O1 124.86(18) . . ? C11 C12 C7 124.23(19) . . ? O1 C12 C7 110.91(17) . . ? C1 O1 C12 105.63(14) . . ? C3 O3 C5 124.25(16) . . ? 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 -179.61(17) . . . . ? C6 C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 O3 -0.1(3) . . . . ? C1 C2 C3 C4 179.56(17) . . . . ? O1 C1 C6 C5 -179.40(15) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? O1 C1 C6 C7 0.4(2) . . . . ? C2 C1 C6 C7 -179.54(16) . . . . ? O2 C5 C6 C1 177.99(19) . . . . ? O3 C5 C6 C1 -1.8(3) . . . . ? O2 C5 C6 C7 -1.7(4) . . . . ? O3 C5 C6 C7 178.51(17) . . . . ? C1 C6 C7 C12 -0.36(19) . . . . ? C5 C6 C7 C12 179.4(2) . . . . ? C1 C6 C7 C8 179.0(2) . . . . ? C5 C6 C7 C8 -1.2(4) . . . . ? C12 C7 C8 C9 -0.1(3) . . . . ? C6 C7 C8 C9 -179.38(19) . . . . ? C7 C8 C9 F1 -179.56(15) . . . . ? C7 C8 C9 C10 -0.3(3) . . . . ? F1 C9 C10 C11 179.97(16) . . . . ? C8 C9 C10 C11 0.7(3) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C10 C11 C12 O1 179.56(16) . . . . ? C10 C11 C12 C7 0.4(3) . . . . ? C8 C7 C12 C11 0.0(3) . . . . ? C6 C7 C12 C11 179.52(18) . . . . ? C8 C7 C12 O1 -179.28(15) . . . . ? C6 C7 C12 O1 0.2(2) . . . . ? C6 C1 O1 C12 -0.3(2) . . . . ? C2 C1 O1 C12 179.68(16) . . . . ? C11 C12 O1 C1 -179.28(17) . . . . ? C7 C12 O1 C1 0.0(2) . . . . ? C2 C3 O3 C5 -1.2(3) . . . . ? C4 C3 O3 C5 179.11(16) . . . . ? O2 C5 O3 C3 -177.70(16) . . . . ? C6 C5 O3 C3 2.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 70.79 _diffrn_measured_fraction_theta_full 0.960 _refine_diff_density_max 0.187 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.061 # Attachment '- ijf0931.cif' data_ijf0931 _database_code_depnum_ccdc_archive 'CCDC 773154' #TrackingRef '- ijf0931.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H7 F O3' _chemical_formula_sum 'C12 H7 F O3' _chemical_formula_weight 218.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 3.7597(2) _cell_length_b 6.1644(4) _cell_length_c 19.6660(11) _cell_angle_alpha 92.543(5) _cell_angle_beta 90.715(5) _cell_angle_gamma 90.125(5) _cell_volume 455.30(5) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3459 _cell_measurement_theta_min 4.5006 _cell_measurement_theta_max 71.0719 _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.591 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 1.095 _exptl_absorpt_correction_T_min 0.58387 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Onyx' _diffrn_detector_area_resol_mean 8.2707 _diffrn_reflns_number 4447 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.5006 _diffrn_reflns_theta_max 71.0719 _reflns_number_total 1706 _reflns_number_gt 1542 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0822P)^2^+0.2098P] 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 SHELXL _refine_ls_extinction_coef 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1706 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0514 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1382 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _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 0.8119(4) 0.6032(3) 0.22680(9) 0.0210(4) Uani 1 1 d . . . C2 C 0.8934(5) 0.7416(3) 0.17363(9) 0.0233(4) Uani 1 1 d . . . H2 H 1.0083 0.8743 0.1815 0.028 Uiso 1 1 calc R . . C3 C 0.7924(5) 0.6674(3) 0.11071(9) 0.0224(4) Uani 1 1 d . . . C4 C 0.8507(5) 0.7818(3) 0.04672(9) 0.0275(4) Uani 1 1 d . . . H4A H 0.9630 0.9195 0.0572 0.041 Uiso 1 1 calc R . . H4B H 0.6260 0.8046 0.0244 0.041 Uiso 1 1 calc R . . H4C H 1.0005 0.6953 0.0172 0.041 Uiso 1 1 calc R . . C5 C 0.5297(5) 0.3326(3) 0.15078(9) 0.0217(4) Uani 1 1 d . . . C6 C 0.6438(4) 0.4070(3) 0.21752(9) 0.0211(4) Uani 1 1 d . . . C7 C 0.6125(4) 0.3190(3) 0.28411(9) 0.0217(4) Uani 1 1 d . . . C8 C 0.4781(5) 0.1284(3) 0.31031(9) 0.0239(4) Uani 1 1 d . . . H8 H 0.3744 0.0210 0.2818 0.029 Uiso 1 1 calc R . . C9 C 0.5040(5) 0.1041(3) 0.37995(9) 0.0270(5) Uani 1 1 d . . . H9 H 0.4196 -0.0214 0.3989 0.032 Uiso 1 1 calc R . . C10 C 0.6561(5) 0.2678(3) 0.42107(9) 0.0278(4) Uani 1 1 d . . . C11 C 0.7923(5) 0.4594(3) 0.39816(9) 0.0260(5) Uani 1 1 d . . . H11 H 0.8917 0.5673 0.4270 0.031 Uiso 1 1 calc R . . C12 C 0.7674(4) 0.4758(3) 0.32860(9) 0.0223(4) Uani 1 1 d . . . F1 F 0.6749(3) 0.2395(2) 0.48944(5) 0.0390(4) Uani 1 1 d . . . O1 O 0.8914(3) 0.6515(2) 0.29376(6) 0.0234(3) Uani 1 1 d . . . O2 O 0.6214(3) 0.4716(2) 0.09927(6) 0.0231(3) Uani 1 1 d . . . O3 O 0.3654(3) 0.1700(2) 0.13384(6) 0.0280(4) 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 0.0251(8) 0.0195(9) 0.0184(8) 0.0007(7) 0.0006(6) 0.0007(7) C2 0.0288(9) 0.0180(9) 0.0231(9) 0.0021(7) 0.0013(7) -0.0018(7) C3 0.0249(8) 0.0181(9) 0.0244(9) 0.0034(7) 0.0018(6) -0.0008(7) C4 0.0342(10) 0.0252(10) 0.0235(9) 0.0065(7) 0.0019(7) -0.0046(8) C5 0.0261(8) 0.0184(9) 0.0209(8) 0.0029(7) 0.0017(6) -0.0010(7) C6 0.0244(8) 0.0188(9) 0.0203(9) 0.0017(7) 0.0007(6) 0.0005(7) C7 0.0251(8) 0.0207(9) 0.0193(9) 0.0005(7) 0.0010(6) 0.0020(7) C8 0.0289(9) 0.0202(10) 0.0226(9) 0.0016(7) 0.0017(7) -0.0005(7) C9 0.0340(10) 0.0230(10) 0.0247(10) 0.0079(7) 0.0037(7) -0.0008(7) C10 0.0359(10) 0.0308(11) 0.0169(9) 0.0040(7) 0.0027(7) 0.0012(8) C11 0.0326(10) 0.0255(10) 0.0199(9) -0.0007(7) 0.0011(7) -0.0004(7) C12 0.0271(9) 0.0188(9) 0.0210(9) 0.0017(7) 0.0024(6) -0.0010(7) F1 0.0604(8) 0.0395(8) 0.0178(6) 0.0076(5) 0.0007(5) -0.0078(6) O1 0.0315(7) 0.0189(7) 0.0198(7) 0.0015(5) -0.0001(5) -0.0038(5) O2 0.0310(7) 0.0194(7) 0.0189(6) 0.0023(5) 0.0007(5) -0.0038(5) O3 0.0391(8) 0.0219(7) 0.0230(7) -0.0001(5) -0.0010(5) -0.0082(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.366(2) . ? C1 C6 1.367(3) . ? C1 C2 1.415(2) . ? C2 C3 1.350(3) . ? C2 H2 0.9300 . ? C3 O2 1.375(2) . ? C3 C4 1.488(2) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 O3 1.208(2) . ? C5 O2 1.401(2) . ? C5 C6 1.431(2) . ? C6 C7 1.446(2) . ? C7 C12 1.396(2) . ? C7 C8 1.400(3) . ? C8 C9 1.386(2) . ? C8 H8 0.9300 . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 F1 1.364(2) . ? C10 C11 1.382(3) . ? C11 C12 1.378(2) . ? C11 H11 0.9300 . ? C12 O1 1.390(2) . ? 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 C6 112.15(15) . . ? O1 C1 C2 123.57(16) . . ? C6 C1 C2 124.28(16) . . ? C3 C2 C1 115.23(17) . . ? C3 C2 H2 122.4 . . ? C1 C2 H2 122.4 . . ? C2 C3 O2 122.28(16) . . ? C2 C3 C4 125.40(18) . . ? O2 C3 C4 112.33(16) . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O3 C5 O2 117.10(16) . . ? O3 C5 C6 128.78(17) . . ? O2 C5 C6 114.12(16) . . ? C1 C6 C5 119.99(16) . . ? C1 C6 C7 106.64(16) . . ? C5 C6 C7 133.34(17) . . ? C12 C7 C8 119.12(16) . . ? C12 C7 C6 104.67(16) . . ? C8 C7 C6 136.20(17) . . ? C9 C8 C7 118.14(17) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C10 C9 C8 119.55(18) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? F1 C10 C11 117.03(17) . . ? F1 C10 C9 118.08(18) . . ? C11 C10 C9 124.89(17) . . ? C12 C11 C10 113.84(17) . . ? C12 C11 H11 123.1 . . ? C10 C11 H11 123.1 . . ? C11 C12 O1 124.29(16) . . ? C11 C12 C7 124.44(17) . . ? O1 C12 C7 111.26(15) . . ? C1 O1 C12 105.27(13) . . ? C3 O2 C5 124.05(14) . . ? 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 -179.57(15) . . . . ? C6 C1 C2 C3 0.0(3) . . . . ? C1 C2 C3 O2 0.2(3) . . . . ? C1 C2 C3 C4 -179.45(16) . . . . ? O1 C1 C6 C5 177.97(14) . . . . ? C2 C1 C6 C5 -1.7(3) . . . . ? O1 C1 C6 C7 -0.37(19) . . . . ? C2 C1 C6 C7 179.98(16) . . . . ? O3 C5 C6 C1 -176.46(17) . . . . ? O2 C5 C6 C1 2.8(2) . . . . ? O3 C5 C6 C7 1.3(3) . . . . ? O2 C5 C6 C7 -179.38(16) . . . . ? C1 C6 C7 C12 0.38(18) . . . . ? C5 C6 C7 C12 -177.64(18) . . . . ? C1 C6 C7 C8 -178.61(19) . . . . ? C5 C6 C7 C8 3.4(3) . . . . ? C12 C7 C8 C9 0.3(2) . . . . ? C6 C7 C8 C9 179.14(18) . . . . ? C7 C8 C9 C10 0.7(3) . . . . ? C8 C9 C10 F1 179.50(15) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? F1 C10 C11 C12 179.40(15) . . . . ? C9 C10 C11 C12 -0.5(3) . . . . ? C10 C11 C12 O1 -178.91(16) . . . . ? C10 C11 C12 C7 1.5(3) . . . . ? C8 C7 C12 C11 -1.5(3) . . . . ? C6 C7 C12 C11 179.32(16) . . . . ? C8 C7 C12 O1 178.92(14) . . . . ? C6 C7 C12 O1 -0.28(18) . . . . ? C6 C1 O1 C12 0.19(18) . . . . ? C2 C1 O1 C12 179.85(16) . . . . ? C11 C12 O1 C1 -179.53(16) . . . . ? C7 C12 O1 C1 0.07(18) . . . . ? C2 C3 O2 C5 1.2(3) . . . . ? C4 C3 O2 C5 -179.09(14) . . . . ? O3 C5 O2 C3 176.72(15) . . . . ? C6 C5 O2 C3 -2.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 71.23 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.331 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.065