# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2 _audit_creation_date 2013-08-12T17:04:30-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 7-(prop-2-in-1-yloxy)-1-benzopyran-2-one ; _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 O3' _chemical_formula_sum 'C12 H8 O3' _chemical_formula_weight 200.18 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.0432(2) _cell_length_b 6.4967(3) _cell_length_c 20.6568(6) _cell_angle_alpha 90 _cell_angle_beta 91.044(3) _cell_angle_gamma 90 _cell_volume 945.05(6) _cell_formula_units_Z 4 _cell_measurement_temperature 170.0(1) _cell_measurement_reflns_used 1489 _cell_measurement_theta_min 2.888 _cell_measurement_theta_max 28.268 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'irregular plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.06 _exptl_crystal_density_diffrn 1.407 _exptl_crystal_F_000 416 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.90445 _exptl_absorpt_correction_T_max 1.00000 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 170.0(1) _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'SuperNova, Single source at offset, Eos' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 16.0107 _diffrn_measurement_method '\w scans' _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_av_R_equivalents 0.0117 _diffrn_reflns_number 2947 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.893 _diffrn_reflns_theta_max 25.499 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _reflns_number_total 1753 _reflns_number_gt 1432 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro, Agilent Technologies, 2013' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies, 2013' _computing_data_reduction 'CrysAlisPro, Agilent Technologies, 2013' _computing_structure_solution 'SIR-2002 (Burla et al., 2003)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+0.4693P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1753 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1347 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.169 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.047 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.21193(18) 0.2362(2) 0.46861(6) 0.0297(4) Uani 1 d . . O2 O 0.2278(2) 0.1126(2) 0.36946(6) 0.0415(4) Uani 1 d . . O3 O 0.12471(18) 0.4904(2) 0.68345(6) 0.0326(4) Uani 1 d . . C2 C 0.2497(3) 0.2629(3) 0.40364(9) 0.0304(5) Uani 1 d . . C3 C 0.3106(3) 0.4645(3) 0.38369(9) 0.0333(5) Uani 1 d . . H3 H 0.3431 0.4865 0.3398 0.04 Uiso 1 calc . . C4 C 0.3226(3) 0.6213(3) 0.42551(9) 0.0316(5) Uani 1 d . . H4 H 0.3628 0.7527 0.4109 0.038 Uiso 1 calc . . C5 C 0.2783(3) 0.7489(3) 0.53918(10) 0.0312(5) Uani 1 d . . H5 H 0.3148 0.8843 0.5273 0.037 Uiso 1 calc . . C6 C 0.2295(3) 0.7095(3) 0.60206(10) 0.0308(5) Uani 1 d . . H6 H 0.2327 0.8168 0.6333 0.037 Uiso 1 calc . . C7 C 0.1750(2) 0.5108(3) 0.61982(8) 0.0264(4) Uani 1 d . . C8 C 0.1699(2) 0.3521(3) 0.57503(8) 0.0254(4) Uani 1 d . . H8 H 0.133 0.217 0.587 0.03 Uiso 1 calc . . C9 C 0.2207(2) 0.3976(3) 0.51179(8) 0.0244(4) Uani 1 d . . C10 C 0.2755(2) 0.5933(3) 0.49221(9) 0.0269(4) Uani 1 d . . C11 C 0.1012(3) 0.2860(3) 0.70840(9) 0.0330(5) Uani 1 d . . H11A H 0.0075 0.2108 0.6811 0.04 Uiso 1 calc . . H11B H 0.0513 0.2937 0.7528 0.04 Uiso 1 calc . . C12 C 0.2816(3) 0.1733(3) 0.70960(8) 0.0312(5) Uani 1 d . . C13 C 0.4299(3) 0.0888(4) 0.70983(10) 0.0407(5) Uani 1 d . . H13 H 0.5493 0.0208 0.71 0.049 Uiso 1 calc . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0364(8) 0.0318(8) 0.0209(7) -0.0009(6) 0.0021(5) 0.0028(6) O2 0.0545(10) 0.0439(10) 0.0261(7) -0.0066(7) 0.0028(6) 0.0106(7) O3 0.0402(8) 0.0341(8) 0.0238(7) -0.0008(6) 0.0054(5) 0.0058(6) C2 0.0276(10) 0.0423(13) 0.0215(9) 0.0007(9) 0.0007(7) 0.0098(8) C3 0.0283(10) 0.0482(14) 0.0236(9) 0.0087(9) 0.0035(7) 0.0074(9) C4 0.0260(10) 0.0378(12) 0.0311(10) 0.0104(9) 0.0026(7) 0.0037(8) C5 0.0276(10) 0.0281(11) 0.0378(11) 0.0042(9) 0.0005(8) 0.0018(8) C6 0.0305(10) 0.0297(11) 0.0320(10) -0.0043(9) -0.0008(7) 0.0040(8) C7 0.0236(9) 0.0330(11) 0.0227(9) 0.0014(8) 0.0006(7) 0.0060(8) C8 0.0267(9) 0.0257(10) 0.0238(9) 0.0027(8) 0.0008(7) 0.0019(8) C9 0.0215(9) 0.0289(11) 0.0227(9) -0.0007(8) -0.0003(7) 0.0056(7) C10 0.0208(9) 0.0322(11) 0.0277(10) 0.0054(8) 0.0011(7) 0.0046(8) C11 0.0369(11) 0.0381(12) 0.0241(10) 0.0018(9) 0.0042(7) -0.0010(9) C12 0.0454(12) 0.0305(11) 0.0178(9) -0.0010(8) 0.0008(7) -0.0009(9) C13 0.0505(13) 0.0422(13) 0.0294(11) 0.0015(10) 0.0015(9) 0.0107(11) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 O1 C9 1.378(2) . ? O1 C2 1.384(2) . ? O2 C2 1.213(2) . ? O3 C7 1.374(2) . ? O3 C11 1.435(2) . ? C2 C3 1.441(3) . ? C3 C4 1.337(3) . ? C3 H3 0.95 . ? C4 C10 1.435(3) . ? C4 H4 0.95 . ? C5 C6 1.374(3) . ? C5 C10 1.401(3) . ? C5 H5 0.95 . ? C6 C7 1.398(3) . ? C6 H6 0.95 . ? C7 C8 1.385(3) . ? C8 C9 1.392(3) . ? C8 H8 0.95 . ? C9 C10 1.391(3) . ? C11 C12 1.466(3) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C13 1.180(3) . ? C13 H13 0.95 . ? 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 C9 O1 C2 121.70(16) . . ? C7 O3 C11 117.77(15) . . ? O2 C2 O1 116.02(19) . . ? O2 C2 C3 126.93(18) . . ? O1 C2 C3 117.06(18) . . ? C4 C3 C2 121.57(18) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C10 120.70(19) . . ? C3 C4 H4 119.7 . . ? C10 C4 H4 119.7 . . ? C6 C5 C10 121.33(19) . . ? C6 C5 H5 119.3 . . ? C10 C5 H5 119.3 . . ? C5 C6 C7 119.65(19) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? O3 C7 C8 124.30(18) . . ? O3 C7 C6 114.63(17) . . ? C8 C7 C6 121.05(17) . . ? C7 C8 C9 117.70(18) . . ? C7 C8 H8 121.1 . . ? C9 C8 H8 121.1 . . ? O1 C9 C8 115.90(17) . . ? O1 C9 C10 121.13(16) . . ? C8 C9 C10 122.96(18) . . ? C9 C10 C5 117.30(17) . . ? C9 C10 C4 117.74(19) . . ? C5 C10 C4 124.96(19) . . ? O3 C11 C12 111.27(16) . . ? O3 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? O3 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108 . . ? C13 C12 C11 177.6(2) . . ? C12 C13 H13 180 . . ? 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 C9 O1 C2 O2 -176.17(15) . . . . ? C9 O1 C2 C3 3.9(2) . . . . ? O2 C2 C3 C4 177.33(19) . . . . ? O1 C2 C3 C4 -2.7(3) . . . . ? C2 C3 C4 C10 0.2(3) . . . . ? C10 C5 C6 C7 -0.2(3) . . . . ? C11 O3 C7 C8 12.7(2) . . . . ? C11 O3 C7 C6 -168.70(16) . . . . ? C5 C6 C7 O3 -178.45(15) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? O3 C7 C8 C9 178.44(15) . . . . ? C6 C7 C8 C9 -0.1(3) . . . . ? C2 O1 C9 C8 176.79(15) . . . . ? C2 O1 C9 C10 -2.6(2) . . . . ? C7 C8 C9 O1 -179.37(15) . . . . ? C7 C8 C9 C10 0.0(3) . . . . ? O1 C9 C10 C5 179.29(14) . . . . ? C8 C9 C10 C5 0.0(3) . . . . ? O1 C9 C10 C4 0.0(3) . . . . ? C8 C9 C10 C4 -179.36(15) . . . . ? C6 C5 C10 C9 0.2(3) . . . . ? C6 C5 C10 C4 179.43(17) . . . . ? C3 C4 C10 C9 1.2(3) . . . . ? C3 C4 C10 C5 -178.10(18) . . . . ? C7 O3 C11 C12 65.4(2) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 955660' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_2a _audit_creation_date 2013-08-12T17:25:58-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; [PPh4][Au{C?CCH2O-7-(prop-2-in-1-yloxy)-1-benzopyran-2-one}2] ; _chemical_melting_point ? _chemical_formula_moiety 'C24 H14 Au O6, C24 H20 P' _chemical_formula_sum 'C48 H34 Au O6 P' _chemical_formula_weight 934.69 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.4254(3) _cell_length_b 12.8050(3) _cell_length_c 14.7713(4) _cell_angle_alpha 98.028(2) _cell_angle_beta 103.649(2) _cell_angle_gamma 95.056(2) _cell_volume 1882.38(9) _cell_formula_units_Z 2 _cell_measurement_temperature 123.0(1) _cell_measurement_reflns_used 12600 _cell_measurement_theta_min 4.396 _cell_measurement_theta_max 76.176 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 1.649 _exptl_crystal_F_000 928 #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 8.175 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) (compiled Feb 1 2013,16:14:44) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.49208 _exptl_absorpt_correction_T_max 1.00000 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 123.0(1) _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_radiation_monochromator mirror _diffrn_detector_area_resol_mean 5.1977 _diffrn_measurement_method '\w scans' _diffrn_reflns_av_unetI/netI 0.0288 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_number 12816 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.122 _diffrn_reflns_theta_max 66.994 _diffrn_reflns_theta_full 67.684 _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.991 _reflns_number_total 6652 _reflns_number_gt 6573 _reflns_threshold_expression 'I > 2\s(I)' #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'CrysAlisPro, Agilent Technologies, 2013' _computing_cell_refinement 'CrysAlisPro, Agilent Technologies, 2013' _computing_data_reduction 'CrysAlisPro, Agilent Technologies, 2013' _computing_structure_solution 'SUPERFLIP (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'MERCURY (Macrae et al., 2006)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0366P)^2^+1.7594P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6652 _refine_ls_number_parameters 505 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0233 _refine_ls_wR_factor_ref 0.0604 _refine_ls_wR_factor_gt 0.0602 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.076 _refine_diff_density_min -1.399 _refine_diff_density_rms 0.084 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Au Au -4.4197 7.298 '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' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_disorder_assembly _atom_site_disorder_group Au1 Au 0.67824(2) 0.28222(2) 0.73088(2) 0.01928(5) Uani 1 d . . O1 O 0.6758(2) 0.70994(16) 0.94096(14) 0.0229(4) Uani 1 d . . O2 O 0.6054(2) 0.82678(18) 0.84988(16) 0.0319(5) Uani 1 d . . O3 O 0.7991(2) 0.42072(16) 1.10032(14) 0.0267(4) Uani 1 d . . O4 O 0.31074(19) 0.08834(17) 0.43040(14) 0.0242(4) Uani 1 d . . O5 O 0.2128(2) -0.06114(16) 0.10356(14) 0.0256(4) Uani 1 d . . O6 O 0.1740(3) -0.1282(2) -0.04750(16) 0.0379(5) Uani 1 d . . C2 C 0.5914(3) 0.7852(2) 0.9161(2) 0.0237(6) Uani 1 d . . C3 C 0.4950(3) 0.8034(2) 0.9705(2) 0.0260(6) Uani 1 d . . H3 H 0.4393 0.8573 0.9581 0.031 Uiso 1 calc . . C4 C 0.4819(3) 0.7463(2) 1.0382(2) 0.0246(6) Uani 1 d . . H4 H 0.4165 0.7595 1.0721 0.03 Uiso 1 calc . . C5 C 0.5548(3) 0.5971(2) 1.1249(2) 0.0264(6) Uani 1 d . . H5 H 0.4909 0.6059 1.1609 0.032 Uiso 1 calc . . C6 C 0.6343(3) 0.5182(2) 1.1374(2) 0.0257(6) Uani 1 d . . H6 H 0.6252 0.4728 1.1817 0.031 Uiso 1 calc . . C7 C 0.7297(3) 0.5039(2) 1.08465(19) 0.0218(6) Uani 1 d . . C8 C 0.7457(3) 0.5718(2) 1.02128(19) 0.0214(6) Uani 1 d . . H8 H 0.8122 0.5649 0.9873 0.026 Uiso 1 calc . . C9 C 0.6625(3) 0.6494(2) 1.00912(19) 0.0198(5) Uani 1 d . . C10 C 0.5661(3) 0.6653(2) 1.0596(2) 0.0217(6) Uani 1 d . . C11 C 0.8962(3) 0.3997(2) 1.0468(2) 0.0258(6) Uani 1 d . . H11A H 0.9472 0.3437 1.0717 0.031 Uiso 1 calc . . H11B H 0.9595 0.4649 1.0561 0.031 Uiso 1 calc . . C12 C 0.8370(3) 0.3654(2) 0.9451(2) 0.0246(6) Uani 1 d . . C13 C 0.7835(3) 0.3371(2) 0.8638(2) 0.0208(6) Uani 1 d . . C14 C 0.5728(3) 0.2239(2) 0.5984(2) 0.0271(6) Uani 1 d . . C15 C 0.5148(3) 0.1821(3) 0.5216(2) 0.0329(7) Uani 1 d . . C16 C 0.4432(3) 0.1256(3) 0.4276(2) 0.0349(8) Uani 1 d . . H16A H 0.4403 0.174 0.3806 0.042 Uiso 1 calc . . H16B H 0.4892 0.0648 0.409 0.042 Uiso 1 calc . . C17 C 0.1268(3) -0.1116(2) 0.0194(2) 0.0284(6) Uani 1 d . . C20 C 0.0054(3) -0.0479(2) 0.2732(2) 0.0210(5) Uani 1 d . . H20 H -0.083 -0.0679 0.2766 0.025 Uiso 1 calc . . C21 C 0.0985(3) 0.0023(2) 0.3529(2) 0.0199(5) Uani 1 d . . H21 H 0.0745 0.0157 0.4112 0.024 Uiso 1 calc . . C22 C 0.2286(3) 0.0339(2) 0.34864(19) 0.0190(5) Uani 1 d . . C23 C 0.2666(3) 0.0117(2) 0.26418(19) 0.0207(5) Uani 1 d . . H23 H 0.3552 0.0318 0.261 0.025 Uiso 1 calc . . C24 C 0.1707(3) -0.0406(2) 0.18487(19) 0.0198(5) Uani 1 d . . C25 C 0.0396(3) -0.0700(2) 0.1862(2) 0.0207(5) Uani 1 d . . P1 P 0.12756(6) 0.73105(5) 0.61328(4) 0.01374(12) Uani 1 d . . C26 C 0.2557(3) 0.6469(2) 0.60809(19) 0.0169(5) Uani 1 d . . C27 C 0.2335(3) 0.5550(2) 0.5409(2) 0.0235(6) Uani 1 d . . H27 H 0.1509 0.5371 0.4948 0.028 Uiso 1 calc . . C28 C 0.3336(3) 0.4895(2) 0.5420(2) 0.0288(7) Uani 1 d . . H28 H 0.3196 0.4273 0.4957 0.035 Uiso 1 calc . . C29 C 0.4530(3) 0.5143(3) 0.6096(3) 0.0308(7) Uani 1 d . . H29 H 0.52 0.4685 0.611 0.037 Uiso 1 calc . . C30 C 0.4744(3) 0.6061(3) 0.6755(2) 0.0307(7) Uani 1 d . . H30 H 0.557 0.6233 0.7216 0.037 Uiso 1 calc . . C31 C 0.3776(3) 0.6732(2) 0.6753(2) 0.0225(6) Uani 1 d . . H31 H 0.3938 0.7366 0.7204 0.027 Uiso 1 calc . . C32 C 0.0255(3) 0.72845(19) 0.49599(19) 0.0167(5) Uani 1 d . . C33 C 0.0823(3) 0.7230(2) 0.4191(2) 0.0197(5) Uani 1 d . . H33 H 0.1755 0.7217 0.4283 0.024 Uiso 1 calc . . C34 C 0.0016(3) 0.7194(2) 0.3288(2) 0.0221(6) Uani 1 d . . H34 H 0.04 0.7166 0.2764 0.027 Uiso 1 calc . . C35 C -0.1350(3) 0.7200(2) 0.3149(2) 0.0244(6) Uani 1 d . . H35 H -0.1901 0.7148 0.2528 0.029 Uiso 1 calc . . C36 C -0.1910(3) 0.7283(2) 0.3919(2) 0.0249(6) Uani 1 d . . H36 H -0.2839 0.7309 0.3826 0.03 Uiso 1 calc . . C37 C -0.1112(3) 0.7326(2) 0.4821(2) 0.0208(5) Uani 1 d . . H37 H -0.1495 0.7384 0.5346 0.025 Uiso 1 calc . . C38 C 0.2074(3) 0.8629(2) 0.66530(19) 0.0162(5) Uani 1 d . . C39 C 0.2403(3) 0.9325(2) 0.60681(19) 0.0184(5) Uani 1 d . . H39 H 0.2105 0.9137 0.5401 0.022 Uiso 1 calc . . C40 C 0.3168(3) 1.0292(2) 0.6472(2) 0.0230(6) Uani 1 d . . H40 H 0.3388 1.0771 0.6079 0.028 Uiso 1 calc . . C41 C 0.3614(3) 1.0566(2) 0.7448(2) 0.0247(6) Uani 1 d . . H41 H 0.4157 1.1222 0.7721 0.03 Uiso 1 calc . . C42 C 0.3263(3) 0.9876(2) 0.8027(2) 0.0248(6) Uani 1 d . . H42 H 0.3549 1.0072 0.8694 0.03 Uiso 1 calc . . C43 C 0.2498(3) 0.8906(2) 0.7633(2) 0.0212(5) Uani 1 d . . H43 H 0.2264 0.8434 0.8027 0.025 Uiso 1 calc . . C44 C 0.0223(3) 0.6825(2) 0.68260(18) 0.0155(5) Uani 1 d . . C45 C -0.0543(3) 0.7507(2) 0.7223(2) 0.0195(5) Uani 1 d . . H45 H -0.0411 0.8248 0.7209 0.023 Uiso 1 calc . . C46 C -0.1498(3) 0.7104(2) 0.76403(19) 0.0198(5) Uani 1 d . . H46 H -0.2032 0.7565 0.7901 0.024 Uiso 1 calc . . C47 C -0.1671(3) 0.6026(2) 0.76741(18) 0.0191(5) Uani 1 d . . H47 H -0.2328 0.5749 0.7956 0.023 Uiso 1 calc . . C48 C -0.0892(3) 0.5347(2) 0.72995(19) 0.0203(5) Uani 1 d . . H48 H -0.101 0.4611 0.7334 0.024 Uiso 1 calc . . C49 C 0.0061(3) 0.5741(2) 0.68734(19) 0.0176(5) Uani 1 d . . H49 H 0.0597 0.5277 0.6617 0.021 Uiso 1 calc . . C19 C -0.0522(3) -0.1201(2) 0.0990(2) 0.0278(6) Uani 1 d . . H19 H -0.1429 -0.1396 0.0974 0.033 Uiso 1 calc . . C18 C -0.0101(3) -0.1394(2) 0.0202(2) 0.0296(6) Uani 1 d . . H18 H -0.0721 -0.1724 -0.0369 0.036 Uiso 1 calc . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Au1 0.01879(7) 0.02353(8) 0.01449(7) 0.00100(4) 0.00486(5) -0.00137(5) O1 0.0236(10) 0.0266(10) 0.0208(10) 0.0062(8) 0.0083(8) 0.0050(8) O2 0.0377(12) 0.0333(11) 0.0293(12) 0.0130(9) 0.0109(10) 0.0093(9) O3 0.0308(11) 0.0304(11) 0.0186(10) 0.0067(8) 0.0036(8) 0.0052(9) O4 0.0203(10) 0.0350(11) 0.0153(9) -0.0010(8) 0.0045(8) 0.0003(8) O5 0.0307(11) 0.0289(10) 0.0162(10) -0.0011(8) 0.0073(8) 0.0017(8) O6 0.0502(14) 0.0446(13) 0.0189(11) -0.0018(9) 0.0127(10) 0.0069(11) C2 0.0224(14) 0.0219(13) 0.0233(14) 0.0004(11) 0.0015(11) 0.0012(11) C3 0.0222(14) 0.0271(15) 0.0271(15) 0.0004(12) 0.0047(12) 0.0049(11) C4 0.0210(14) 0.0280(14) 0.0231(14) -0.0033(11) 0.0078(11) 0.0000(11) C5 0.0255(14) 0.0330(15) 0.0206(14) -0.0005(12) 0.0106(12) -0.0022(12) C6 0.0292(15) 0.0299(15) 0.0172(14) 0.0035(11) 0.0071(12) -0.0032(12) C7 0.0239(14) 0.0223(13) 0.0143(13) -0.0005(10) -0.0009(11) -0.0025(11) C8 0.0190(13) 0.0276(14) 0.0165(13) 0.0013(11) 0.0049(10) 0.0001(11) C9 0.0204(13) 0.0224(13) 0.0136(12) 0.0006(10) 0.0018(10) -0.0028(10) C10 0.0181(13) 0.0250(14) 0.0183(13) -0.0033(11) 0.0034(11) -0.0032(11) C11 0.0242(14) 0.0279(15) 0.0224(15) 0.0035(11) -0.0002(12) 0.0062(12) C12 0.0247(14) 0.0236(14) 0.0265(17) 0.0060(12) 0.0062(12) 0.0056(11) C13 0.0235(14) 0.0232(13) 0.0165(14) 0.0038(11) 0.0060(11) 0.0036(11) C14 0.0222(14) 0.0340(16) 0.0226(16) -0.0071(12) 0.0116(12) -0.0071(12) C15 0.0239(15) 0.0485(19) 0.0269(18) 0.0042(15) 0.0109(13) -0.0018(14) C16 0.0222(15) 0.058(2) 0.0198(15) -0.0051(14) 0.0083(12) -0.0084(14) C17 0.0385(17) 0.0256(14) 0.0187(15) 0.0001(11) 0.0040(13) 0.0065(13) C20 0.0217(13) 0.0173(12) 0.0260(15) 0.0069(10) 0.0076(11) 0.0034(10) C21 0.0244(14) 0.0196(12) 0.0196(13) 0.0067(10) 0.0098(11) 0.0070(11) C22 0.0227(14) 0.0185(12) 0.0160(13) 0.0038(10) 0.0039(11) 0.0044(10) C23 0.0208(13) 0.0232(13) 0.0195(14) 0.0043(11) 0.0071(11) 0.0035(11) C24 0.0261(14) 0.0188(12) 0.0160(13) 0.0041(10) 0.0061(11) 0.0064(11) C25 0.0243(14) 0.0154(12) 0.0221(14) 0.0026(10) 0.0047(11) 0.0042(10) P1 0.0138(3) 0.0130(3) 0.0153(3) 0.0032(2) 0.0047(2) 0.0020(2) C26 0.0172(12) 0.0168(12) 0.0206(13) 0.0075(10) 0.0085(10) 0.0046(10) C27 0.0231(14) 0.0200(13) 0.0284(15) 0.0033(11) 0.0094(12) 0.0021(11) C28 0.0360(17) 0.0177(13) 0.0404(18) 0.0053(12) 0.0226(14) 0.0076(12) C29 0.0301(16) 0.0310(16) 0.0440(19) 0.0197(14) 0.0218(14) 0.0169(13) C30 0.0223(15) 0.0401(17) 0.0347(17) 0.0147(14) 0.0091(13) 0.0118(13) C31 0.0213(14) 0.0270(14) 0.0217(14) 0.0072(11) 0.0076(11) 0.0054(11) C32 0.0182(13) 0.0127(11) 0.0180(13) 0.0021(9) 0.0031(10) 0.0005(9) C33 0.0228(14) 0.0165(12) 0.0211(14) 0.0035(10) 0.0068(11) 0.0048(10) C34 0.0322(15) 0.0177(12) 0.0182(13) 0.0052(10) 0.0072(11) 0.0060(11) C35 0.0297(15) 0.0179(13) 0.0209(14) 0.0051(10) -0.0032(11) 0.0018(11) C36 0.0182(13) 0.0234(14) 0.0314(16) 0.0080(12) 0.0011(12) 0.0018(11) C37 0.0192(13) 0.0205(13) 0.0235(14) 0.0053(11) 0.0063(11) 0.0025(10) C38 0.0154(12) 0.0145(12) 0.0192(13) 0.0022(10) 0.0051(10) 0.0037(9) C39 0.0201(13) 0.0193(12) 0.0172(13) 0.0033(10) 0.0066(10) 0.0044(10) C40 0.0254(14) 0.0183(13) 0.0287(15) 0.0068(11) 0.0120(12) 0.0023(11) C41 0.0224(14) 0.0165(13) 0.0328(16) -0.0002(11) 0.0048(12) 0.0010(11) C42 0.0296(15) 0.0220(13) 0.0196(14) 0.0006(11) 0.0013(12) 0.0045(11) C43 0.0255(14) 0.0189(13) 0.0200(14) 0.0063(10) 0.0055(11) 0.0042(11) C44 0.0143(12) 0.0180(12) 0.0145(12) 0.0045(9) 0.0033(10) 0.0016(9) C45 0.0221(13) 0.0166(12) 0.0223(14) 0.0061(10) 0.0082(11) 0.0046(10) C46 0.0179(12) 0.0245(14) 0.0187(13) 0.0046(11) 0.0061(10) 0.0063(10) C47 0.0157(12) 0.0266(14) 0.0145(12) 0.0061(10) 0.0023(10) -0.0006(10) C48 0.0230(14) 0.0171(12) 0.0198(13) 0.0033(10) 0.0051(11) -0.0016(10) C49 0.0201(13) 0.0166(12) 0.0167(13) 0.0031(10) 0.0056(10) 0.0018(10) C19 0.0272(15) 0.0243(14) 0.0287(16) 0.0008(12) 0.0024(12) 0.0035(12) C18 0.0324(16) 0.0291(15) 0.0215(15) -0.0035(12) -0.0001(12) 0.0041(12) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 Au1 C13 2.004(3) . ? Au1 C14 2.007(3) . ? O1 C9 1.378(3) . ? O1 C2 1.390(3) . ? O2 C2 1.209(4) . ? O3 C7 1.356(4) . ? O3 C11 1.444(4) . ? O4 C22 1.360(3) . ? O4 C16 1.433(4) . ? O5 C24 1.373(3) . ? O5 C17 1.383(4) . ? O6 C17 1.205(4) . ? C2 C3 1.441(4) . ? C3 C4 1.344(4) . ? C3 H3 0.95 . ? C4 C10 1.439(4) . ? C4 H4 0.95 . ? C5 C6 1.367(4) . ? C5 C10 1.405(4) . ? C5 H5 0.95 . ? C6 C7 1.409(4) . ? C6 H6 0.95 . ? C7 C8 1.391(4) . ? C8 C9 1.378(4) . ? C8 H8 0.95 . ? C9 C10 1.399(4) . ? C11 C12 1.470(4) . ? C11 H11A 0.99 . ? C11 H11B 0.99 . ? C12 C13 1.188(4) . ? C14 C15 1.178(5) . ? C15 C16 1.464(4) . ? C16 H16A 0.99 . ? C16 H16B 0.99 . ? C17 C18 1.444(5) . ? C20 C21 1.371(4) . ? C20 C25 1.410(4) . ? C20 H20 0.95 . ? C21 C22 1.399(4) . ? C21 H21 0.95 . ? C22 C23 1.396(4) . ? C23 C24 1.390(4) . ? C23 H23 0.95 . ? C24 C25 1.391(4) . ? C25 C19 1.437(4) . ? P1 C38 1.795(3) . ? P1 C44 1.797(3) . ? P1 C26 1.797(3) . ? P1 C32 1.801(3) . ? C26 C27 1.394(4) . ? C26 C31 1.396(4) . ? C27 C28 1.394(4) . ? C27 H27 0.95 . ? C28 C29 1.379(5) . ? C28 H28 0.95 . ? C29 C30 1.382(5) . ? C29 H29 0.95 . ? C30 C31 1.382(4) . ? C30 H30 0.95 . ? C31 H31 0.95 . ? C32 C33 1.396(4) . ? C32 C37 1.398(4) . ? C33 C34 1.391(4) . ? C33 H33 0.95 . ? C34 C35 1.392(4) . ? C34 H34 0.95 . ? C35 C36 1.391(4) . ? C35 H35 0.95 . ? C36 C37 1.384(4) . ? C36 H36 0.95 . ? C37 H37 0.95 . ? C38 C43 1.394(4) . ? C38 C39 1.401(4) . ? C39 C40 1.385(4) . ? C39 H39 0.95 . ? C40 C41 1.390(4) . ? C40 H40 0.95 . ? C41 C42 1.395(4) . ? C41 H41 0.95 . ? C42 C43 1.387(4) . ? C42 H42 0.95 . ? C43 H43 0.95 . ? C44 C49 1.397(4) . ? C44 C45 1.395(4) . ? C45 C46 1.387(4) . ? C45 H45 0.95 . ? C46 C47 1.386(4) . ? C46 H46 0.95 . ? C47 C48 1.386(4) . ? C47 H47 0.95 . ? C48 C49 1.390(4) . ? C48 H48 0.95 . ? C49 H49 0.95 . ? C19 C18 1.338(5) . ? C19 H19 0.95 . ? C18 H18 0.95 . ? 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 C13 Au1 C14 178.71(11) . . ? C9 O1 C2 122.2(2) . . ? C7 O3 C11 118.0(2) . . ? C22 O4 C16 116.9(2) . . ? C24 O5 C17 121.6(2) . . ? O2 C2 O1 116.2(3) . . ? O2 C2 C3 127.1(3) . . ? O1 C2 C3 116.8(3) . . ? C4 C3 C2 121.8(3) . . ? C4 C3 H3 119.1 . . ? C2 C3 H3 119.1 . . ? C3 C4 C10 120.5(3) . . ? C3 C4 H4 119.8 . . ? C10 C4 H4 119.8 . . ? C6 C5 C10 121.1(3) . . ? C6 C5 H5 119.5 . . ? C10 C5 H5 119.5 . . ? C5 C6 C7 120.2(3) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? O3 C7 C8 124.9(3) . . ? O3 C7 C6 115.0(2) . . ? C8 C7 C6 120.1(3) . . ? C9 C8 C7 118.2(3) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? O1 C9 C8 116.2(2) . . ? O1 C9 C10 120.6(3) . . ? C8 C9 C10 123.2(3) . . ? C9 C10 C5 117.2(3) . . ? C9 C10 C4 118.0(3) . . ? C5 C10 C4 124.8(3) . . ? O3 C11 C12 113.4(2) . . ? O3 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? O3 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C13 C12 C11 176.9(3) . . ? C12 C13 Au1 174.3(3) . . ? C15 C14 Au1 174.7(3) . . ? C14 C15 C16 177.5(4) . . ? O4 C16 C15 108.5(2) . . ? O4 C16 H16A 110 . . ? C15 C16 H16A 110 . . ? O4 C16 H16B 110 . . ? C15 C16 H16B 110 . . ? H16A C16 H16B 108.4 . . ? O6 C17 O5 116.6(3) . . ? O6 C17 C18 126.4(3) . . ? O5 C17 C18 117.1(3) . . ? C21 C20 C25 120.7(3) . . ? C21 C20 H20 119.6 . . ? C25 C20 H20 119.6 . . ? C20 C21 C22 120.3(3) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? O4 C22 C23 123.9(2) . . ? O4 C22 C21 115.5(2) . . ? C23 C22 C21 120.6(3) . . ? C24 C23 C22 117.8(3) . . ? C24 C23 H23 121.1 . . ? C22 C23 H23 121.1 . . ? O5 C24 C23 115.8(2) . . ? O5 C24 C25 121.3(3) . . ? C23 C24 C25 122.9(3) . . ? C24 C25 C20 117.6(3) . . ? C24 C25 C19 118.0(3) . . ? C20 C25 C19 124.3(3) . . ? C38 P1 C44 110.79(12) . . ? C38 P1 C26 107.64(12) . . ? C44 P1 C26 109.95(12) . . ? C38 P1 C32 111.18(12) . . ? C44 P1 C32 107.70(12) . . ? C26 P1 C32 109.58(13) . . ? C27 C26 C31 120.1(3) . . ? C27 C26 P1 121.2(2) . . ? C31 C26 P1 118.6(2) . . ? C26 C27 C28 119.4(3) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 120.3 . . ? C29 C28 C27 120.5(3) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C28 C29 C30 119.7(3) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C29 C30 C31 121.1(3) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C30 C31 C26 119.3(3) . . ? C30 C31 H31 120.4 . . ? C26 C31 H31 120.4 . . ? C33 C32 C37 119.9(3) . . ? C33 C32 P1 120.3(2) . . ? C37 C32 P1 119.8(2) . . ? C34 C33 C32 119.5(3) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C35 C34 C33 120.3(3) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C36 C35 C34 120.0(3) . . ? C36 C35 H35 120 . . ? C34 C35 H35 120 . . ? C37 C36 C35 120.0(3) . . ? C37 C36 H36 120 . . ? C35 C36 H36 120 . . ? C36 C37 C32 120.2(3) . . ? C36 C37 H37 119.9 . . ? C32 C37 H37 119.9 . . ? C43 C38 C39 120.6(2) . . ? C43 C38 P1 119.8(2) . . ? C39 C38 P1 119.2(2) . . ? C40 C39 C38 119.4(3) . . ? C40 C39 H39 120.3 . . ? C38 C39 H39 120.3 . . ? C39 C40 C41 120.4(3) . . ? C39 C40 H40 119.8 . . ? C41 C40 H40 119.8 . . ? C40 C41 C42 119.9(3) . . ? C40 C41 H41 120 . . ? C42 C41 H41 120 . . ? C43 C42 C41 120.3(3) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C42 C43 C38 119.4(3) . . ? C42 C43 H43 120.3 . . ? C38 C43 H43 120.3 . . ? C49 C44 C45 120.2(2) . . ? C49 C44 P1 119.6(2) . . ? C45 C44 P1 119.81(19) . . ? C46 C45 C44 119.9(2) . . ? C46 C45 H45 120 . . ? C44 C45 H45 120 . . ? C45 C46 C47 119.7(3) . . ? C45 C46 H46 120.1 . . ? C47 C46 H46 120.1 . . ? C48 C47 C46 120.6(2) . . ? C48 C47 H47 119.7 . . ? C46 C47 H47 119.7 . . ? C47 C48 C49 120.2(2) . . ? C47 C48 H48 119.9 . . ? C49 C48 H48 119.9 . . ? C48 C49 C44 119.3(2) . . ? C48 C49 H49 120.4 . . ? C44 C49 H49 120.4 . . ? C18 C19 C25 120.1(3) . . ? C18 C19 H19 120 . . ? C25 C19 H19 120 . . ? C19 C18 C17 121.9(3) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? 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 C9 O1 C2 O2 -173.8(3) . . . . ? C9 O1 C2 C3 4.9(4) . . . . ? O2 C2 C3 C4 174.7(3) . . . . ? O1 C2 C3 C4 -3.8(4) . . . . ? C2 C3 C4 C10 1.0(4) . . . . ? C10 C5 C6 C7 0.1(4) . . . . ? C11 O3 C7 C8 -0.7(4) . . . . ? C11 O3 C7 C6 178.4(2) . . . . ? C5 C6 C7 O3 -177.6(3) . . . . ? C5 C6 C7 C8 1.6(4) . . . . ? O3 C7 C8 C9 176.4(2) . . . . ? C6 C7 C8 C9 -2.7(4) . . . . ? C2 O1 C9 C8 174.8(2) . . . . ? C2 O1 C9 C10 -3.1(4) . . . . ? C7 C8 C9 O1 -175.6(2) . . . . ? C7 C8 C9 C10 2.2(4) . . . . ? O1 C9 C10 C5 177.1(2) . . . . ? C8 C9 C10 C5 -0.6(4) . . . . ? O1 C9 C10 C4 0.0(4) . . . . ? C8 C9 C10 C4 -177.7(3) . . . . ? C6 C5 C10 C9 -0.6(4) . . . . ? C6 C5 C10 C4 176.4(3) . . . . ? C3 C4 C10 C9 1.0(4) . . . . ? C3 C4 C10 C5 -175.9(3) . . . . ? C7 O3 C11 C12 -66.3(3) . . . . ? C22 O4 C16 C15 179.8(3) . . . . ? C24 O5 C17 O6 -178.4(3) . . . . ? C24 O5 C17 C18 1.5(4) . . . . ? C25 C20 C21 C22 1.1(4) . . . . ? C16 O4 C22 C23 0.8(4) . . . . ? C16 O4 C22 C21 -177.5(3) . . . . ? C20 C21 C22 O4 176.3(2) . . . . ? C20 C21 C22 C23 -2.1(4) . . . . ? O4 C22 C23 C24 -177.2(2) . . . . ? C21 C22 C23 C24 1.2(4) . . . . ? C17 O5 C24 C23 -179.2(2) . . . . ? C17 O5 C24 C25 0.3(4) . . . . ? C22 C23 C24 O5 -179.7(2) . . . . ? C22 C23 C24 C25 0.8(4) . . . . ? O5 C24 C25 C20 178.7(2) . . . . ? C23 C24 C25 C20 -1.8(4) . . . . ? O5 C24 C25 C19 -1.8(4) . . . . ? C23 C24 C25 C19 177.6(3) . . . . ? C21 C20 C25 C24 0.9(4) . . . . ? C21 C20 C25 C19 -178.6(3) . . . . ? C38 P1 C26 C27 -154.0(2) . . . . ? C44 P1 C26 C27 85.2(2) . . . . ? C32 P1 C26 C27 -33.0(3) . . . . ? C38 P1 C26 C31 28.4(2) . . . . ? C44 P1 C26 C31 -92.4(2) . . . . ? C32 P1 C26 C31 149.4(2) . . . . ? C31 C26 C27 C28 0.4(4) . . . . ? P1 C26 C27 C28 -177.2(2) . . . . ? C26 C27 C28 C29 1.0(4) . . . . ? C27 C28 C29 C30 -1.5(5) . . . . ? C28 C29 C30 C31 0.6(5) . . . . ? C29 C30 C31 C26 0.8(4) . . . . ? C27 C26 C31 C30 -1.3(4) . . . . ? P1 C26 C31 C30 176.4(2) . . . . ? C38 P1 C32 C33 82.4(2) . . . . ? C44 P1 C32 C33 -156.1(2) . . . . ? C26 P1 C32 C33 -36.5(2) . . . . ? C38 P1 C32 C37 -97.2(2) . . . . ? C44 P1 C32 C37 24.3(2) . . . . ? C26 P1 C32 C37 143.9(2) . . . . ? C37 C32 C33 C34 -1.4(4) . . . . ? P1 C32 C33 C34 179.0(2) . . . . ? C32 C33 C34 C35 -0.8(4) . . . . ? C33 C34 C35 C36 2.4(4) . . . . ? C34 C35 C36 C37 -2.0(4) . . . . ? C35 C36 C37 C32 -0.2(4) . . . . ? C33 C32 C37 C36 1.8(4) . . . . ? P1 C32 C37 C36 -178.6(2) . . . . ? C44 P1 C38 C43 37.1(2) . . . . ? C26 P1 C38 C43 -83.2(2) . . . . ? C32 P1 C38 C43 156.8(2) . . . . ? C44 P1 C38 C39 -150.3(2) . . . . ? C26 P1 C38 C39 89.4(2) . . . . ? C32 P1 C38 C39 -30.6(2) . . . . ? C43 C38 C39 C40 0.7(4) . . . . ? P1 C38 C39 C40 -171.8(2) . . . . ? C38 C39 C40 C41 0.5(4) . . . . ? C39 C40 C41 C42 -1.6(4) . . . . ? C40 C41 C42 C43 1.6(4) . . . . ? C41 C42 C43 C38 -0.5(4) . . . . ? C39 C38 C43 C42 -0.7(4) . . . . ? P1 C38 C43 C42 171.8(2) . . . . ? C38 P1 C44 C49 -147.2(2) . . . . ? C26 P1 C44 C49 -28.4(3) . . . . ? C32 P1 C44 C49 91.0(2) . . . . ? C38 P1 C44 C45 40.0(3) . . . . ? C26 P1 C44 C45 158.9(2) . . . . ? C32 P1 C44 C45 -81.7(2) . . . . ? C49 C44 C45 C46 -2.1(4) . . . . ? P1 C44 C45 C46 170.6(2) . . . . ? C44 C45 C46 C47 1.1(4) . . . . ? C45 C46 C47 C48 0.3(4) . . . . ? C46 C47 C48 C49 -0.9(4) . . . . ? C47 C48 C49 C44 -0.1(4) . . . . ? C45 C44 C49 C48 1.6(4) . . . . ? P1 C44 C49 C48 -171.1(2) . . . . ? C24 C25 C19 C18 1.6(4) . . . . ? C20 C25 C19 C18 -179.0(3) . . . . ? C25 C19 C18 C17 0.2(5) . . . . ? O6 C17 C18 C19 178.2(3) . . . . ? O5 C17 C18 C19 -1.7(4) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 955661'