# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_import _database_code_depnum_ccdc_archive 'CCDC 873362' #TrackingRef 'Chem Comm cmp 1.cif.cif' _audit_creation_date 2011-10-06T10:22:50-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H14 O4 P2' _chemical_formula_sum 'C18 H14 O4 P2' _chemical_formula_weight 356.23 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 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 12.0985(9) _cell_length_b 7.6709(3) _cell_length_c 18.3347(13) _cell_angle_alpha 90 _cell_angle_beta 100.317(2) _cell_angle_gamma 90 _cell_volume 1674.07(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 6247 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 27.485 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Rod _exptl_crystal_colour white _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.9536 _exptl_absorpt_correction_T_max 1.0054 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 0.757579E-1 _diffrn_orient_matrix_ub_12 -0.563531E-1 _diffrn_orient_matrix_ub_13 0.90122E-2 _diffrn_orient_matrix_ub_21 0.67278E-2 _diffrn_orient_matrix_ub_22 0.220999E-1 _diffrn_orient_matrix_ub_23 0.543693E-1 _diffrn_orient_matrix_ub_31 -0.356886E-1 _diffrn_orient_matrix_ub_32 -0.115457 _diffrn_orient_matrix_ub_33 0.60082E-2 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_unetI/netI 0.0658 _diffrn_reflns_number 8193 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_full 27.5 _diffrn_measured_fraction_theta_full 0.982 _diffrn_measured_fraction_theta_max 0.982 _reflns_number_total 3776 _reflns_number_gt 2648 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0847P)^2^+0.2056P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3776 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.053 _refine_ls_wR_factor_ref 0.1699 _refine_ls_wR_factor_gt 0.1334 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.413 _refine_diff_density_min -0.387 _refine_diff_density_rms 0.11 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0955(2) 0.1294(4) 0.16325(16) 0.0354(7) Uani 1 1 d . . . C2 C 0.2075(2) 0.0443(3) 0.16831(15) 0.0325(6) Uani 1 1 d . . . C3 C 0.3064(2) 0.1412(3) 0.18001(15) 0.0302(6) Uani 1 1 d . . . H3 H 0.3034 0.2637 0.1868 0.036 Uiso 1 1 calc R . . C4 C 0.4094(2) 0.0595(3) 0.18177(15) 0.0328(6) Uani 1 1 d . . . C5 C 0.4125(3) -0.1218(4) 0.17473(16) 0.0392(7) Uani 1 1 d . . . H5 H 0.4827 -0.1794 0.1779 0.047 Uiso 1 1 calc R . . C6 C 0.3148(3) -0.2177(4) 0.16321(17) 0.0431(7) Uani 1 1 d . . . H6 H 0.318 -0.3407 0.1579 0.052 Uiso 1 1 calc R . . C7 C 0.2123(3) -0.1364(3) 0.15932(16) 0.0383(7) Uani 1 1 d . . . H7 H 0.145 -0.203 0.1505 0.046 Uiso 1 1 calc R . . C8 C 0.5160(2) 0.1617(4) 0.18943(16) 0.0368(7) Uani 1 1 d . . . C9 C 0.4938(2) 0.3182(3) 0.05018(17) 0.0349(6) Uani 1 1 d . . . C10 C 0.3814(2) 0.2557(3) 0.01161(15) 0.0322(6) Uani 1 1 d . . . C11 C 0.2820(2) 0.3120(3) 0.03298(15) 0.0315(6) Uani 1 1 d . . . H11 H 0.2848 0.3975 0.0708 0.038 Uiso 1 1 calc R . . C12 C 0.1795(2) 0.2438(4) -0.00067(15) 0.0337(6) Uani 1 1 d . . . C13 C 0.1755(3) 0.1229(4) -0.05817(18) 0.0446(8) Uani 1 1 d . . . H13 H 0.1054 0.0769 -0.082 0.054 Uiso 1 1 calc R . . C14 C 0.2739(3) 0.0703(4) -0.08023(18) 0.0495(8) Uani 1 1 d . . . H14 H 0.2711 -0.0108 -0.1197 0.059 Uiso 1 1 calc R . . C15 C 0.3755(3) 0.1347(4) -0.04546(17) 0.0404(7) Uani 1 1 d . . . H15 H 0.4425 0.0962 -0.0605 0.049 Uiso 1 1 calc R . . C16 C 0.0723(2) 0.2912(4) 0.02417(16) 0.0376(7) Uani 1 1 d . . . C17 C -0.0695(3) 0.3882(5) 0.12517(19) 0.0482(8) Uani 1 1 d . . . H17A H -0.0928 0.5043 0.1059 0.072 Uiso 1 1 calc R . . H17B H -0.083 0.3775 0.1761 0.072 Uiso 1 1 calc R . . H17C H -0.113 0.2993 0.094 0.072 Uiso 1 1 calc R . . C18 C 0.6533(3) 0.4518(4) 0.1707(2) 0.0545(9) Uani 1 1 d . . . H18A H 0.6717 0.493 0.2221 0.082 Uiso 1 1 calc R . . H18B H 0.6676 0.5451 0.1371 0.082 Uiso 1 1 calc R . . H18C H 0.7 0.3505 0.1644 0.082 Uiso 1 1 calc R . . O1 O 0.01774(17) 0.0567(3) 0.18377(12) 0.0446(5) Uani 1 1 d . . . O2 O 0.60542(18) 0.1023(3) 0.21759(13) 0.0532(6) Uani 1 1 d . . . O3 O 0.57498(18) 0.3235(3) 0.01923(13) 0.0489(6) Uani 1 1 d . . . O4 O -0.01692(18) 0.2899(3) -0.01805(12) 0.0552(6) Uani 1 1 d . . . P1 P 0.07894(6) 0.35799(10) 0.12408(4) 0.0350(2) Uani 1 1 d . . . P2 P 0.50611(6) 0.39025(9) 0.14968(5) 0.0367(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 0.0339(16) 0.0426(15) 0.0286(15) -0.0059(12) 0.0026(12) -0.0030(12) C2 0.0361(15) 0.0346(14) 0.0275(14) -0.0005(11) 0.0074(11) 0.0009(12) C3 0.0332(14) 0.0311(13) 0.0266(14) 0.0001(10) 0.0060(11) 0.0039(11) C4 0.0355(16) 0.0369(14) 0.0266(14) 0.0032(11) 0.0074(12) 0.0049(12) C5 0.0466(18) 0.0375(15) 0.0358(17) 0.0064(12) 0.0134(14) 0.0139(13) C6 0.059(2) 0.0293(14) 0.0418(17) -0.0005(12) 0.0126(15) 0.0050(14) C7 0.0483(18) 0.0351(15) 0.0306(16) 0.0030(11) 0.0045(13) -0.0053(13) C8 0.0344(16) 0.0415(16) 0.0358(16) 0.0023(12) 0.0096(13) 0.0080(13) C9 0.0345(16) 0.0283(13) 0.0440(17) 0.0053(12) 0.0130(13) 0.0072(11) C10 0.0377(15) 0.0320(13) 0.0287(14) 0.0057(11) 0.0102(12) 0.0054(11) C11 0.0354(15) 0.0310(13) 0.0284(14) -0.0013(11) 0.0069(12) 0.0043(11) C12 0.0364(16) 0.0366(14) 0.0274(14) -0.0019(11) 0.0037(12) 0.0038(12) C13 0.0437(18) 0.0488(18) 0.0388(18) -0.0092(13) 0.0008(14) 0.0000(14) C14 0.055(2) 0.0526(18) 0.0421(19) -0.0154(15) 0.0110(16) 0.0079(16) C15 0.0465(18) 0.0427(16) 0.0348(17) 0.0006(13) 0.0144(14) 0.0107(14) C16 0.0322(16) 0.0445(16) 0.0354(16) -0.0028(13) 0.0039(13) -0.0020(13) C17 0.0351(17) 0.069(2) 0.0423(19) 0.0018(15) 0.0116(14) 0.0142(15) C18 0.0350(18) 0.054(2) 0.072(3) 0.0011(17) 0.0024(16) -0.0067(15) O1 0.0349(12) 0.0556(13) 0.0438(13) -0.0021(10) 0.0087(9) -0.0105(10) O2 0.0324(12) 0.0665(15) 0.0596(16) 0.0203(11) 0.0053(11) 0.0127(10) O3 0.0400(13) 0.0536(13) 0.0584(15) 0.0064(11) 0.0232(11) 0.0031(10) O4 0.0342(12) 0.0862(17) 0.0411(13) -0.0086(12) -0.0039(10) 0.0016(11) P1 0.0296(4) 0.0422(4) 0.0335(4) -0.0024(3) 0.0062(3) 0.0064(3) P2 0.0296(4) 0.0351(4) 0.0443(5) -0.0023(3) 0.0037(3) 0.0014(3) #----------------------------------------------------------------------------# # 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 C1 O1 1.211(3) . ? C1 C2 1.492(4) . ? C1 P1 1.892(3) . ? C2 C3 1.391(4) . ? C2 C7 1.398(4) . ? C3 C4 1.390(4) . ? C3 H3 0.95 . ? C4 C5 1.398(4) . ? C4 C8 1.495(4) . ? C5 C6 1.376(4) . ? C5 H5 0.95 . ? C6 C7 1.378(4) . ? C6 H6 0.95 . ? C7 H7 0.95 . ? C8 O2 1.202(3) . ? C8 P2 1.894(3) . ? C9 O3 1.220(3) . ? C9 C10 1.495(4) . ? C9 P2 1.886(3) . ? C10 C15 1.391(4) . ? C10 C11 1.398(4) . ? C11 C12 1.385(4) . ? C11 H11 0.95 . ? C12 C13 1.398(4) . ? C12 C16 1.495(4) . ? C13 C14 1.384(4) . ? C13 H13 0.95 . ? C14 C15 1.371(4) . ? C14 H14 0.95 . ? C15 H15 0.95 . ? C16 O4 1.210(3) . ? C16 P1 1.890(3) . ? C17 P1 1.815(3) . ? C17 H17A 0.98 . ? C17 H17B 0.98 . ? C17 H17C 0.98 . ? C18 P2 1.816(3) . ? C18 H18A 0.98 . ? C18 H18B 0.98 . ? C18 H18C 0.98 . ? 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 C2 121.8(3) . . ? O1 C1 P1 120.6(2) . . ? C2 C1 P1 117.6(2) . . ? C3 C2 C7 119.7(3) . . ? C3 C2 C1 121.4(2) . . ? C7 C2 C1 118.9(3) . . ? C4 C3 C2 120.3(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 119.0(3) . . ? C3 C4 C8 121.4(2) . . ? C5 C4 C8 119.6(2) . . ? C6 C5 C4 120.6(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C5 C6 C7 120.4(3) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C6 C7 C2 119.9(3) . . ? C6 C7 H7 120 . . ? C2 C7 H7 120 . . ? O2 C8 C4 122.5(3) . . ? O2 C8 P2 120.4(2) . . ? C4 C8 P2 117.08(19) . . ? O3 C9 C10 122.0(3) . . ? O3 C9 P2 120.6(2) . . ? C10 C9 P2 117.3(2) . . ? C15 C10 C11 119.1(3) . . ? C15 C10 C9 119.3(3) . . ? C11 C10 C9 121.6(2) . . ? C12 C11 C10 120.3(3) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 119.6(3) . . ? C11 C12 C16 121.9(2) . . ? C13 C12 C16 118.4(3) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.3(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C10 120.8(3) . . ? C14 C15 H15 119.6 . . ? C10 C15 H15 119.6 . . ? O4 C16 C12 121.7(3) . . ? O4 C16 P1 120.1(2) . . ? C12 C16 P1 118.2(2) . . ? P1 C17 H17A 109.5 . . ? P1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? P1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? P2 C18 H18A 109.5 . . ? P2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? P2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 P1 C16 100.06(14) . . ? C17 P1 C1 98.76(14) . . ? C16 P1 C1 95.73(13) . . ? C18 P2 C9 100.73(15) . . ? C18 P2 C8 99.60(14) . . ? C9 P2 C8 95.14(12) . . ? data_jun711 _database_code_depnum_ccdc_archive 'CCDC 873363' #TrackingRef 'Chem Comm cmpd2.cif.cif' _audit_creation_date 2011-06-29T09:26:14-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.2 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H28 Cl2 O8 P4 Pt, 2(C4 H8 O)' _chemical_formula_sum 'C44 H44 Cl2 O10 P4 Pt' _chemical_formula_weight 1122.65 _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 10.4564(4) _cell_length_b 11.3437(6) _cell_length_c 11.5627(7) _cell_angle_alpha 87.512(3) _cell_angle_beta 69.834(3) _cell_angle_gamma 64.064(3) _cell_volume 1148.36(10) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 34327 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 26.733 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description Rhombohedral _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.18 _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 3.366 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.2635 _exptl_absorpt_correction_T_max 0.3095 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_source 'Enraf Nonius FR590' _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector 'CCD plate' _diffrn_orient_matrix_type 'by Bruker AXS Collect from scalepack cell' _diffrn_orient_matrix_ub_11 -0.105302 _diffrn_orient_matrix_ub_12 0.7833E-2 _diffrn_orient_matrix_ub_13 0.255312E-1 _diffrn_orient_matrix_ub_21 0.386815E-1 _diffrn_orient_matrix_ub_22 -0.763859E-1 _diffrn_orient_matrix_ub_23 -0.636761E-1 _diffrn_orient_matrix_ub_31 0.208948E-1 _diffrn_orient_matrix_ub_32 -0.622199E-1 _diffrn_orient_matrix_ub_33 0.626222E-1 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_reflns_av_R_equivalents 0.0482 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_number 15427 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.49 _diffrn_reflns_theta_max 26.79 _diffrn_reflns_theta_full 26.79 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 4843 _reflns_number_gt 4812 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; The THF solvate was disordered over two positions. The bond lengths and angles for each component were restrained to be equal using the SAME command 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^)+(0.0409P)^2^+0.3959P] 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_number_reflns 4843 _refine_ls_number_parameters 324 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0264 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0653 _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 1.621 _refine_diff_density_min -1.468 _refine_diff_density_rms 0.101 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pt Pt -1.7033 8.3905 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pt Pt 0 0.5 0.5 0.02177(6) Uani 1 2 d S . . Cl Cl 0.06967(9) 0.38660(8) 0.65632(7) 0.03881(19) Uani 1 1 d . . . P1 P 0.23928(8) 0.48571(7) 0.40433(7) 0.02551(16) Uani 1 1 d . . . P2 P 0.11102(10) 0.10133(9) 0.31814(9) 0.03560(19) Uani 1 1 d . . . O1 O 0.3383(4) 0.5692(3) 0.1891(3) 0.0547(7) Uani 1 1 d . . . O2 O 0.2002(4) 0.0347(3) 0.0720(3) 0.0558(7) Uani 1 1 d . . . O3 O 0.3086(3) -0.1295(2) 0.3640(3) 0.0501(7) Uani 1 1 d . . . O4 O 0.4690(4) 0.3781(3) 0.4852(4) 0.0691(10) Uani 1 1 d . . . C1 C 0.2507(4) 0.6283(3) 0.4513(3) 0.0360(7) Uani 1 1 d . . . H1A H 0.2177 0.6413 0.542 0.054 Uiso 1 1 calc R . . H1B H 0.1844 0.7064 0.4235 0.054 Uiso 1 1 calc R . . H1C H 0.3563 0.6152 0.4141 0.054 Uiso 1 1 calc R . . C2 C 0.3073(4) 0.4810(3) 0.2292(3) 0.0336(7) Uani 1 1 d . . . C3 C 0.3280(4) 0.3717(3) 0.1477(3) 0.0329(7) Uani 1 1 d . . . C4 C 0.2474(4) 0.2981(3) 0.1861(3) 0.0296(6) Uani 1 1 d . . . H4 H 0.1705 0.3203 0.2666 0.035 Uiso 1 1 calc R . . C5 C 0.2792(4) 0.1917(3) 0.1069(3) 0.0324(7) Uani 1 1 d . . . C6 C 0.3875(5) 0.1635(4) -0.0127(3) 0.0466(9) Uani 1 1 d . . . H6 H 0.4081 0.0923 -0.0678 0.056 Uiso 1 1 calc R . . C7 C 0.4651(5) 0.2385(4) -0.0516(4) 0.0541(11) Uani 1 1 d . . . H7 H 0.5383 0.2194 -0.1335 0.065 Uiso 1 1 calc R . . C8 C 0.4365(4) 0.3415(4) 0.0286(3) 0.0447(9) Uani 1 1 d . . . H8 H 0.4915 0.3918 0.002 0.054 Uiso 1 1 calc R . . C9 C 0.2049(4) 0.1035(3) 0.1466(3) 0.0360(7) Uani 1 1 d . . . C10 C 0.0349(5) -0.0136(4) 0.3090(5) 0.0531(10) Uani 1 1 d . . . H10A H -0.0407 0.0244 0.2691 0.08 Uiso 1 1 calc R . . H10B H -0.0137 -0.03 0.3929 0.08 Uiso 1 1 calc R . . H10C H 0.1181 -0.0971 0.2601 0.08 Uiso 1 1 calc R . . C11 C 0.2889(4) -0.0174(3) 0.3474(3) 0.0336(7) Uani 1 1 d . . . C12 C 0.3978(4) 0.0305(3) 0.3537(3) 0.0291(6) Uani 1 1 d . . . C13 C 0.3493(4) 0.1629(3) 0.3894(3) 0.0276(6) Uani 1 1 d . . . H13 H 0.2451 0.2245 0.4099 0.033 Uiso 1 1 calc R . . C14 C 0.4531(4) 0.2051(3) 0.3950(3) 0.0303(6) Uani 1 1 d . . . C15 C 0.6058(4) 0.1155(3) 0.3649(3) 0.0365(7) Uani 1 1 d . . . H15 H 0.677 0.145 0.3678 0.044 Uiso 1 1 calc R . . C16 C 0.6538(4) -0.0165(4) 0.3307(4) 0.0403(8) Uani 1 1 d . . . H16 H 0.7581 -0.0779 0.3104 0.048 Uiso 1 1 calc R . . C17 C 0.5512(4) -0.0598(3) 0.3259(3) 0.0368(7) Uani 1 1 d . . . H17 H 0.5845 -0.1509 0.3037 0.044 Uiso 1 1 calc R . . C18 C 0.4048(4) 0.3457(3) 0.4342(4) 0.0360(7) Uani 1 1 d . . . O5 O -0.1623(9) 0.2621(6) 0.1951(6) 0.082(2) Uani 0.608(10) 1 d PD A 1 C19 C -0.177(2) 0.3886(11) 0.1718(14) 0.089(5) Uani 0.608(10) 1 d PD A 1 H19A H -0.1314 0.4182 0.2195 0.107 Uiso 0.608(10) 1 calc PR A 1 H19B H -0.2854 0.4533 0.194 0.107 Uiso 0.608(10) 1 calc PR A 1 C20 C -0.088(2) 0.373(2) 0.030(2) 0.114(9) Uani 0.608(10) 1 d PD A 1 H20A H -0.1418 0.4502 -0.0078 0.137 Uiso 0.608(10) 1 calc PR A 1 H20B H 0.0165 0.3609 0.0124 0.137 Uiso 0.608(10) 1 calc PR A 1 C21 C -0.085(2) 0.256(2) -0.0170(15) 0.100(6) Uani 0.608(10) 1 d PD A 1 H21A H 0.0217 0.189 -0.0605 0.12 Uiso 0.608(10) 1 calc PR A 1 H21B H -0.1385 0.2775 -0.0768 0.12 Uiso 0.608(10) 1 calc PR A 1 C22 C -0.160(2) 0.2047(16) 0.0864(12) 0.094(5) Uani 0.608(10) 1 d PD A 1 H22A H -0.265 0.2291 0.0915 0.113 Uiso 0.608(10) 1 calc PR A 1 H22B H -0.103 0.1072 0.0772 0.113 Uiso 0.608(10) 1 calc PR A 1 O5A O -0.3441(15) 0.3392(13) 0.1818(12) 0.108(5) Uani 0.392(10) 1 d PD A 2 C19A C -0.300(3) 0.4331(19) 0.2049(15) 0.091(6) Uani 0.392(10) 1 d PD A 2 H19C H -0.2825 0.4233 0.2845 0.109 Uiso 0.392(10) 1 calc PR A 2 H19D H -0.3806 0.5234 0.2104 0.109 Uiso 0.392(10) 1 calc PR A 2 C20A C -0.150(4) 0.411(3) 0.097(3) 0.118(12) Uani 0.392(10) 1 d PD A 2 H20C H -0.1613 0.4919 0.0571 0.141 Uiso 0.392(10) 1 calc PR A 2 H20D H -0.0634 0.3806 0.1253 0.141 Uiso 0.392(10) 1 calc PR A 2 C21A C -0.131(3) 0.309(3) 0.013(2) 0.125(17) Uani 0.392(10) 1 d PD A 2 H21C H -0.0215 0.245 -0.0253 0.15 Uiso 0.392(10) 1 calc PR A 2 H21D H -0.1684 0.3478 -0.0543 0.15 Uiso 0.392(10) 1 calc PR A 2 C22A C -0.218(3) 0.244(2) 0.085(2) 0.123(13) Uani 0.392(10) 1 d PD A 2 H22C H -0.2527 0.2078 0.0329 0.148 Uiso 0.392(10) 1 calc PR A 2 H22D H -0.1539 0.1701 0.1207 0.148 Uiso 0.392(10) 1 calc PR 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 Pt 0.02208(9) 0.02076(9) 0.02262(9) 0.00493(6) -0.00486(6) -0.01243(6) Cl 0.0362(4) 0.0413(4) 0.0291(4) 0.0129(3) -0.0112(3) -0.0103(4) P1 0.0228(4) 0.0234(3) 0.0309(4) 0.0062(3) -0.0060(3) -0.0140(3) P2 0.0312(4) 0.0334(4) 0.0394(5) 0.0007(4) -0.0050(4) -0.0177(4) O1 0.071(2) 0.0499(16) 0.0429(15) 0.0120(12) -0.0004(14) -0.0431(15) O2 0.072(2) 0.0559(17) 0.0488(16) -0.0042(13) -0.0220(15) -0.0362(16) O3 0.0669(18) 0.0317(13) 0.0648(18) 0.0157(12) -0.0273(15) -0.0315(13) O4 0.068(2) 0.0385(15) 0.130(3) 0.0080(17) -0.071(2) -0.0227(14) C1 0.0369(18) 0.0261(15) 0.047(2) 0.0039(14) -0.0118(15) -0.0182(14) C2 0.0294(16) 0.0338(16) 0.0331(17) 0.0070(13) -0.0027(13) -0.0171(14) C3 0.0318(16) 0.0296(15) 0.0301(16) 0.0087(13) -0.0053(13) -0.0125(13) C4 0.0284(15) 0.0295(15) 0.0261(15) 0.0047(12) -0.0064(13) -0.0117(13) C5 0.0335(17) 0.0284(15) 0.0289(16) 0.0041(12) -0.0103(14) -0.0092(13) C6 0.058(2) 0.0349(18) 0.0315(18) -0.0007(14) -0.0073(17) -0.0136(17) C7 0.061(3) 0.044(2) 0.0288(18) 0.0012(16) 0.0090(18) -0.0183(19) C8 0.046(2) 0.0384(18) 0.0337(19) 0.0078(15) 0.0038(16) -0.0193(16) C9 0.0351(17) 0.0316(16) 0.0364(18) -0.0010(14) -0.0120(15) -0.0112(14) C10 0.049(2) 0.054(2) 0.068(3) 0.006(2) -0.017(2) -0.036(2) C11 0.0414(18) 0.0300(16) 0.0274(16) 0.0025(12) -0.0063(14) -0.0188(14) C12 0.0363(17) 0.0268(14) 0.0240(15) 0.0066(12) -0.0077(13) -0.0167(13) C13 0.0298(15) 0.0251(14) 0.0270(15) 0.0067(12) -0.0090(13) -0.0130(12) C14 0.0326(16) 0.0277(15) 0.0333(16) 0.0090(12) -0.0128(13) -0.0157(13) C15 0.0308(17) 0.0358(17) 0.0416(19) 0.0102(14) -0.0147(15) -0.0132(14) C16 0.0311(17) 0.0355(17) 0.045(2) 0.0064(15) -0.0140(16) -0.0072(14) C17 0.0421(19) 0.0261(15) 0.0309(17) 0.0030(13) -0.0087(15) -0.0092(14) C18 0.0307(17) 0.0288(16) 0.050(2) 0.0080(14) -0.0166(15) -0.0140(14) O5 0.119(6) 0.071(4) 0.059(4) 0.017(3) -0.030(4) -0.048(4) C19 0.112(12) 0.056(6) 0.122(13) 0.023(7) -0.071(11) -0.035(7) C20 0.097(13) 0.15(2) 0.131(16) 0.103(15) -0.070(12) -0.073(13) C21 0.096(13) 0.113(13) 0.080(9) 0.024(9) -0.047(9) -0.027(12) C22 0.119(13) 0.090(9) 0.083(9) 0.004(6) -0.057(9) -0.039(9) O5A 0.110(10) 0.098(9) 0.109(10) -0.018(7) -0.008(8) -0.062(8) C19A 0.121(16) 0.111(14) 0.092(12) 0.048(10) -0.056(12) -0.087(13) C20A 0.11(2) 0.101(19) 0.15(4) 0.05(2) -0.05(2) -0.048(18) C21A 0.072(16) 0.12(3) 0.11(2) 0.05(2) -0.006(13) 0.001(18) C22A 0.099(18) 0.076(15) 0.19(3) 0.008(16) -0.065(19) -0.021(14) #----------------------------------------------------------------------------# # 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 Pt P1 2.2940(7) 2_566 ? Pt P1 2.2940(7) . ? Pt Cl 2.3106(7) . ? Pt Cl 2.3106(7) 2_566 ? P1 C1 1.793(3) . ? P1 C2 1.896(3) . ? P1 C18 1.897(3) . ? P2 C10 1.823(4) . ? P2 C9 1.890(4) . ? P2 C11 1.895(4) . ? O1 C2 1.208(4) . ? O2 C9 1.215(4) . ? O3 C11 1.214(4) . ? O4 C18 1.201(4) . ? C1 H1A 0.98 . ? C1 H1B 0.98 . ? C1 H1C 0.98 . ? C2 C3 1.482(5) . ? C3 C8 1.387(5) . ? C3 C4 1.390(5) . ? C4 C5 1.394(5) . ? C4 H4 0.95 . ? C5 C6 1.392(5) . ? C5 C9 1.486(5) . ? C6 C7 1.380(6) . ? C6 H6 0.95 . ? C7 C8 1.382(6) . ? C7 H7 0.95 . ? C8 H8 0.95 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C10 H10C 0.98 . ? C11 C12 1.484(5) . ? C12 C13 1.388(4) . ? C12 C17 1.400(5) . ? C13 C14 1.385(4) . ? C13 H13 0.95 . ? C14 C15 1.390(5) . ? C14 C18 1.485(4) . ? C15 C16 1.382(5) . ? C15 H15 0.95 . ? C16 C17 1.378(5) . ? C16 H16 0.95 . ? C17 H17 0.95 . ? O5 C19 1.400(12) . ? O5 C22 1.427(12) . ? C19 C20 1.56(2) . ? C19 H19A 0.99 . ? C19 H19B 0.99 . ? C20 C21 1.43(2) . ? C20 H20A 0.99 . ? C20 H20B 0.99 . ? C21 C22 1.439(15) . ? C21 H21A 0.99 . ? C21 H21B 0.99 . ? C22 H22A 0.99 . ? C22 H22B 0.99 . ? O5A C19A 1.401(15) . ? O5A C22A 1.413(17) . ? C19A C20A 1.55(3) . ? C19A H19C 0.99 . ? C19A H19D 0.99 . ? C20A C21A 1.44(3) . ? C20A H20C 0.99 . ? C20A H20D 0.99 . ? C21A C22A 1.442(18) . ? C21A H21C 0.99 . ? C21A H21D 0.99 . ? C22A H22C 0.99 . ? C22A H22D 0.99 . ? 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 P1 Pt P1 180 2_566 . ? P1 Pt Cl 88.95(3) 2_566 . ? P1 Pt Cl 91.05(3) . . ? P1 Pt Cl 91.05(3) 2_566 2_566 ? P1 Pt Cl 88.95(3) . 2_566 ? Cl Pt Cl 180 . 2_566 ? C1 P1 C2 101.81(16) . . ? C1 P1 C18 102.03(16) . . ? C2 P1 C18 104.56(16) . . ? C1 P1 Pt 111.96(12) . . ? C2 P1 Pt 116.16(11) . . ? C18 P1 Pt 118.20(11) . . ? C10 P2 C9 99.22(19) . . ? C10 P2 C11 98.74(18) . . ? C9 P2 C11 97.65(15) . . ? P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 122.8(3) . . ? O1 C2 P1 115.6(3) . . ? C3 C2 P1 121.5(2) . . ? C8 C3 C4 119.6(3) . . ? C8 C3 C2 117.2(3) . . ? C4 C3 C2 123.2(3) . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120 . . ? C5 C4 H4 120 . . ? C6 C5 C4 119.5(3) . . ? C6 C5 C9 118.2(3) . . ? C4 C5 C9 122.3(3) . . ? C7 C6 C5 120.3(4) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.0(3) . . ? C6 C7 H7 120 . . ? C8 C7 H7 120 . . ? C7 C8 C3 120.5(4) . . ? C7 C8 H8 119.8 . . ? C3 C8 H8 119.8 . . ? O2 C9 C5 121.9(3) . . ? O2 C9 P2 119.1(3) . . ? C5 C9 P2 119.1(2) . . ? P2 C10 H10A 109.5 . . ? P2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? P2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O3 C11 C12 121.7(3) . . ? O3 C11 P2 119.2(3) . . ? C12 C11 P2 119.0(2) . . ? C13 C12 C17 119.6(3) . . ? C13 C12 C11 121.0(3) . . ? C17 C12 C11 119.4(3) . . ? C14 C13 C12 119.9(3) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.4(3) . . ? C13 C14 C18 121.3(3) . . ? C15 C14 C18 118.4(3) . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 120.4(3) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C12 120.0(3) . . ? C16 C17 H17 120 . . ? C12 C17 H17 120 . . ? O4 C18 C14 122.3(3) . . ? O4 C18 P1 115.7(3) . . ? C14 C18 P1 121.9(2) . . ? C19 O5 C22 105.9(9) . . ? O5 C19 C20 104.2(11) . . ? O5 C19 H19A 110.9 . . ? C20 C19 H19A 110.9 . . ? O5 C19 H19B 110.9 . . ? C20 C19 H19B 110.9 . . ? H19A C19 H19B 108.9 . . ? C21 C20 C19 103.6(12) . . ? C21 C20 H20A 111 . . ? C19 C20 H20A 111 . . ? C21 C20 H20B 111 . . ? C19 C20 H20B 111 . . ? H20A C20 H20B 109 . . ? C20 C21 C22 108.2(15) . . ? C20 C21 H21A 110.1 . . ? C22 C21 H21A 110.1 . . ? C20 C21 H21B 110.1 . . ? C22 C21 H21B 110.1 . . ? H21A C21 H21B 108.4 . . ? O5 C22 C21 106.5(11) . . ? O5 C22 H22A 110.4 . . ? C21 C22 H22A 110.4 . . ? O5 C22 H22B 110.4 . . ? C21 C22 H22B 110.4 . . ? H22A C22 H22B 108.6 . . ? C19A O5A C22A 106.4(14) . . ? O5A C19A C20A 108.1(14) . . ? O5A C19A H19C 110.1 . . ? C20A C19A H19C 110.1 . . ? O5A C19A H19D 110.1 . . ? C20A C19A H19D 110.1 . . ? H19C C19A H19D 108.4 . . ? C21A C20A C19A 102.5(15) . . ? C21A C20A H20C 111.3 . . ? C19A C20A H20C 111.3 . . ? C21A C20A H20D 111.3 . . ? C19A C20A H20D 111.3 . . ? H20C C20A H20D 109.2 . . ? C20A C21A C22A 106.6(19) . . ? C20A C21A H21C 110.4 . . ? C22A C21A H21C 110.4 . . ? C20A C21A H21D 110.4 . . ? C22A C21A H21D 110.4 . . ? H21C C21A H21D 108.6 . . ? O5A C22A C21A 107.4(16) . . ? O5A C22A H22C 110.2 . . ? C21A C22A H22C 110.2 . . ? O5A C22A H22D 110.2 . . ? C21A C22A H22D 110.2 . . ? H22C C22A H22D 108.5 . . ? #===END