# 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_jlf3752 #TrackingRef '6185_web_deposit_cif_file_0_JasonFreeman_1310079035.jlf3752.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H20 O6 P2 S2' _chemical_formula_weight 626.54 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' S S 0.1246 0.1234 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.5662(17) _cell_length_b 14.881(3) _cell_length_c 11.645(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.53(3) _cell_angle_gamma 90.00 _cell_volume 1449.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.436 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3184 _diffrn_reflns_av_R_equivalents 0.1227 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 1 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2543 _reflns_number_gt 2003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1178P)^2^+0.1318P] 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(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2543 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0820 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1700 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.001 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 0.4254(4) 0.2514(3) 0.9393(3) 0.0547(9) Uani 1 1 d . . . C2 C 0.4751(5) 0.1704(4) 0.9017(4) 0.0730(12) Uani 1 1 d . . . H2 H 0.4238 0.1468 0.8294 0.088 Uiso 1 1 calc R . . C3 C 0.6005(6) 0.1245(4) 0.9711(5) 0.0913(16) Uani 1 1 d . . . H3 H 0.6336 0.0695 0.9467 0.110 Uiso 1 1 calc R . . C4 C 0.6758(6) 0.1611(5) 1.0767(5) 0.0976(19) Uani 1 1 d . . . H4 H 0.7626 0.1315 1.1231 0.117 Uiso 1 1 calc R . . C5 C 0.6246(5) 0.2414(4) 1.1152(4) 0.0795(14) Uani 1 1 d . . . H5 H 0.6761 0.2643 1.1878 0.095 Uiso 1 1 calc R . . C6 C 0.4971(4) 0.2890(3) 1.0472(3) 0.0594(10) Uani 1 1 d . . . C7 C 0.4417(5) 0.3761(3) 1.0859(3) 0.0604(10) Uani 1 1 d . . . C8 C 0.5497(7) 0.4411(4) 1.1402(4) 0.0872(17) Uani 1 1 d . . . H8 H 0.6587 0.4296 1.1512 0.105 Uiso 1 1 calc R . . C9 C 0.5003(10) 0.5221(4) 1.1782(4) 0.105(2) Uani 1 1 d . . . H9 H 0.5750 0.5639 1.2156 0.126 Uiso 1 1 calc R . . C10 C 0.3385(10) 0.5403(3) 1.1601(4) 0.102(2) Uani 1 1 d . . . H10 H 0.3047 0.5954 1.1836 0.122 Uiso 1 1 calc R . . C11 C 0.2271(7) 0.4782(3) 1.1077(4) 0.0736(12) Uani 1 1 d . . . H11 H 0.1183 0.4903 1.0959 0.088 Uiso 1 1 calc R . . C12 C 0.2801(5) 0.3981(2) 1.0733(3) 0.0541(9) Uani 1 1 d . . . C13 C 0.0629(4) 0.1927(2) 0.9028(3) 0.0426(7) Uani 1 1 d . . . C14 C 0.0026(4) 0.1373(2) 0.8103(3) 0.0502(9) Uani 1 1 d . . . H14 H -0.0165 0.1554 0.7320 0.060 Uiso 1 1 calc R . . C15 C -0.0272(4) 0.0501(2) 0.8464(3) 0.0490(8) Uani 1 1 d . . . H15 H -0.0679 0.0041 0.7944 0.059 Uiso 1 1 calc R . . C16 C 0.0096(3) 0.0398(2) 0.9657(3) 0.0393(7) Uani 1 1 d . . . O1 O 0.3017(3) 0.29800(17) 0.86417(19) 0.0516(7) Uani 1 1 d . . . O2 O 0.1653(3) 0.33149(16) 1.02885(19) 0.0485(6) Uani 1 1 d . . . O3 O 0.0276(3) 0.36247(16) 0.8109(2) 0.0623(7) Uani 1 1 d . . . P P 0.13001(10) 0.30363(6) 0.89431(7) 0.0434(3) Uani 1 1 d . . . S S 0.08425(11) 0.13737(5) 1.03466(7) 0.0470(3) 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 0.0522(19) 0.074(3) 0.0400(18) 0.0088(16) 0.0148(14) -0.0069(18) C2 0.074(3) 0.096(3) 0.055(2) -0.006(2) 0.026(2) 0.011(2) C3 0.085(3) 0.118(4) 0.076(3) 0.003(3) 0.031(3) 0.038(3) C4 0.070(3) 0.153(6) 0.075(3) 0.023(3) 0.026(2) 0.040(3) C5 0.062(2) 0.125(4) 0.050(2) 0.011(2) 0.0066(18) -0.005(3) C6 0.058(2) 0.077(3) 0.0438(19) 0.0059(18) 0.0131(16) -0.0169(19) C7 0.082(3) 0.065(2) 0.0334(17) 0.0029(16) 0.0099(16) -0.031(2) C8 0.106(3) 0.107(4) 0.045(2) 0.005(2) 0.007(2) -0.061(3) C9 0.172(6) 0.084(4) 0.055(3) -0.009(3) 0.017(3) -0.085(4) C10 0.195(7) 0.054(3) 0.062(3) -0.018(2) 0.040(4) -0.051(4) C11 0.126(4) 0.047(2) 0.051(2) -0.0076(17) 0.028(2) -0.015(2) C12 0.086(3) 0.0417(19) 0.0326(17) -0.0022(13) 0.0088(15) -0.0241(18) C13 0.0467(17) 0.0395(17) 0.0394(17) 0.0031(13) 0.0045(12) -0.0030(14) C14 0.069(2) 0.0397(19) 0.0393(18) 0.0032(13) 0.0053(15) -0.0047(15) C15 0.064(2) 0.0349(17) 0.0452(18) -0.0038(13) 0.0062(14) -0.0080(15) C16 0.0424(15) 0.0297(15) 0.0449(17) -0.0028(12) 0.0079(12) -0.0030(12) O1 0.0665(16) 0.0513(15) 0.0367(12) 0.0035(10) 0.0106(10) -0.0157(11) O2 0.0628(14) 0.0429(13) 0.0404(13) -0.0018(10) 0.0124(10) -0.0092(11) O3 0.0857(18) 0.0411(15) 0.0548(15) 0.0123(11) 0.0034(12) 0.0051(12) P 0.0594(6) 0.0317(5) 0.0369(5) 0.0035(3) 0.0057(4) -0.0059(3) S 0.0662(6) 0.0351(5) 0.0379(5) 0.0005(3) 0.0074(4) -0.0135(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 1.381(6) . ? C1 C6 1.390(5) . ? C1 O1 1.402(4) . ? C2 C3 1.377(6) . ? C2 H2 0.9300 . ? C3 C4 1.372(8) . ? C3 H3 0.9300 . ? C4 C5 1.380(8) . ? C4 H4 0.9300 . ? C5 C6 1.395(6) . ? C5 H5 0.9300 . ? C6 C7 1.484(6) . ? C7 C8 1.392(6) . ? C7 C12 1.398(6) . ? C8 C9 1.382(8) . ? C8 H8 0.9300 . ? C9 C10 1.382(9) . ? C9 H9 0.9300 . ? C10 C11 1.373(7) . ? C10 H10 0.9300 . ? C11 C12 1.366(6) . ? C11 H11 0.9300 . ? C12 O2 1.413(4) . ? C13 C14 1.366(5) . ? C13 S 1.717(3) . ? C13 P 1.757(3) . ? C14 C15 1.405(5) . ? C14 H14 0.9300 . ? C15 C16 1.365(4) . ? C15 H15 0.9300 . ? C16 C16 1.457(6) 3_557 ? C16 S 1.715(3) . ? O1 P 1.587(3) . ? O2 P 1.585(2) . ? O3 P 1.452(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 122.1(4) . . ? C2 C1 O1 118.5(3) . . ? C6 C1 O1 119.4(4) . . ? C3 C2 C1 120.2(4) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 118.9(5) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 121.0(5) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 121.3(5) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 116.6(4) . . ? C1 C6 C7 121.2(4) . . ? C5 C6 C7 122.2(4) . . ? C8 C7 C12 115.5(4) . . ? C8 C7 C6 121.3(4) . . ? C12 C7 C6 123.1(3) . . ? C9 C8 C7 122.1(5) . . ? C9 C8 H8 118.9 . . ? C7 C8 H8 118.9 . . ? C10 C9 C8 119.2(5) . . ? C10 C9 H9 120.4 . . ? C8 C9 H9 120.4 . . ? C11 C10 C9 120.8(5) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 118.3(5) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C11 C12 C7 123.9(4) . . ? C11 C12 O2 118.0(4) . . ? C7 C12 O2 118.0(3) . . ? C14 C13 S 111.4(3) . . ? C14 C13 P 126.5(3) . . ? S C13 P 121.91(19) . . ? C13 C14 C15 112.6(3) . . ? C13 C14 H14 123.7 . . ? C15 C14 H14 123.7 . . ? C16 C15 C14 113.1(3) . . ? C16 C15 H15 123.5 . . ? C14 C15 H15 123.5 . . ? C15 C16 C16 128.4(3) . 3_557 ? C15 C16 S 111.2(2) . . ? C16 C16 S 120.4(3) 3_557 . ? C1 O1 P 119.97(19) . . ? C12 O2 P 120.91(19) . . ? O3 P O2 117.46(15) . . ? O3 P O1 109.79(15) . . ? O2 P O1 104.19(13) . . ? O3 P C13 116.51(15) . . ? O2 P C13 100.62(14) . . ? O1 P C13 107.05(14) . . ? C16 S C13 91.80(15) . . ? 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 -0.8(6) . . . . ? O1 C1 C2 C3 177.4(4) . . . . ? C1 C2 C3 C4 -0.8(8) . . . . ? C2 C3 C4 C5 1.9(8) . . . . ? C3 C4 C5 C6 -1.4(8) . . . . ? C2 C1 C6 C5 1.3(6) . . . . ? O1 C1 C6 C5 -176.9(3) . . . . ? C2 C1 C6 C7 -179.9(3) . . . . ? O1 C1 C6 C7 1.9(5) . . . . ? C4 C5 C6 C1 -0.2(6) . . . . ? C4 C5 C6 C7 -179.0(4) . . . . ? C1 C6 C7 C8 -137.6(4) . . . . ? C5 C6 C7 C8 41.1(5) . . . . ? C1 C6 C7 C12 43.8(5) . . . . ? C5 C6 C7 C12 -137.5(4) . . . . ? C12 C7 C8 C9 -0.4(5) . . . . ? C6 C7 C8 C9 -179.1(4) . . . . ? C7 C8 C9 C10 -1.3(7) . . . . ? C8 C9 C10 C11 1.7(7) . . . . ? C9 C10 C11 C12 -0.4(7) . . . . ? C10 C11 C12 C7 -1.4(6) . . . . ? C10 C11 C12 O2 174.6(3) . . . . ? C8 C7 C12 C11 1.8(5) . . . . ? C6 C7 C12 C11 -179.5(3) . . . . ? C8 C7 C12 O2 -174.2(3) . . . . ? C6 C7 C12 O2 4.5(5) . . . . ? S C13 C14 C15 0.4(4) . . . . ? P C13 C14 C15 174.7(3) . . . . ? C13 C14 C15 C16 0.3(5) . . . . ? C14 C15 C16 C16 178.1(4) . . . 3_557 ? C14 C15 C16 S -0.9(4) . . . . ? C2 C1 O1 P 108.5(3) . . . . ? C6 C1 O1 P -73.2(4) . . . . ? C11 C12 O2 P 111.1(3) . . . . ? C7 C12 O2 P -72.7(3) . . . . ? C12 O2 P O3 -79.1(3) . . . . ? C12 O2 P O1 42.5(3) . . . . ? C12 O2 P C13 153.3(3) . . . . ? C1 O1 P O3 174.2(3) . . . . ? C1 O1 P O2 47.6(3) . . . . ? C1 O1 P C13 -58.4(3) . . . . ? C14 C13 P O3 46.1(4) . . . . ? S C13 P O3 -140.1(2) . . . . ? C14 C13 P O2 174.3(3) . . . . ? S C13 P O2 -11.9(2) . . . . ? C14 C13 P O1 -77.2(3) . . . . ? S C13 P O1 96.6(2) . . . . ? C15 C16 S C13 0.9(3) . . . . ? C16 C16 S C13 -178.2(3) 3_557 . . . ? C14 C13 S C16 -0.7(3) . . . . ? P C13 S C16 -175.4(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.540 _refine_diff_density_min -0.485 _refine_diff_density_rms 0.091 _database_code_depnum_ccdc_archive 'CCDC 833334' ####################################################################### # # 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_jlf3355 #TrackingRef '6186_web_deposit_cif_file_1_JasonFreeman_1310079035.JLF3355.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H20 O4 P2 S2 Se2' _chemical_formula_weight 752.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.0929 2.2259 '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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.1023(14) _cell_length_b 12.956(3) _cell_length_c 15.763(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.46(3) _cell_angle_gamma 90.00 _cell_volume 1443.9(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.731 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 2.855 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.1774 _exptl_absorpt_correction_T_max 0.3286 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3502 _diffrn_reflns_av_R_equivalents 0.0623 _diffrn_reflns_av_sigmaI/netI 0.1009 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 24.97 _reflns_number_total 2536 _reflns_number_gt 1526 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.1021P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0080(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2536 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1298 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1846 _refine_ls_wR_factor_gt 0.1583 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.8224(9) 0.2734(6) 0.1609(5) 0.0386(16) Uani 1 1 d . . . C2 C 0.8302(11) 0.1862(6) 0.1123(5) 0.049(2) Uani 1 1 d . . . H2 H 0.9258 0.1381 0.1252 0.059 Uiso 1 1 calc R . . C3 C 0.6982(13) 0.1695(7) 0.0449(5) 0.057(2) Uani 1 1 d . . . H3 H 0.7005 0.1092 0.0129 0.068 Uiso 1 1 calc R . . C4 C 0.5610(12) 0.2435(8) 0.0249(5) 0.063(2) Uani 1 1 d . . . H4 H 0.4740 0.2343 -0.0224 0.076 Uiso 1 1 calc R . . C5 C 0.5514(10) 0.3305(7) 0.0741(5) 0.052(2) Uani 1 1 d . . . H5 H 0.4558 0.3783 0.0602 0.062 Uiso 1 1 calc R . . C6 C 0.6802(9) 0.3485(5) 0.1434(4) 0.0344(16) Uani 1 1 d . . . C7 C 0.6691(9) 0.4429(5) 0.1953(5) 0.0369(16) Uani 1 1 d . . . C8 C 0.6181(10) 0.5375(6) 0.1567(5) 0.048(2) Uani 1 1 d . . . H8 H 0.5954 0.5409 0.0976 0.057 Uiso 1 1 calc R . . C9 C 0.6009(11) 0.6252(6) 0.2043(6) 0.054(2) Uani 1 1 d . . . H9 H 0.5656 0.6872 0.1775 0.064 Uiso 1 1 calc R . . C10 C 0.6356(10) 0.6213(6) 0.2904(6) 0.051(2) Uani 1 1 d . . . H10 H 0.6236 0.6807 0.3226 0.061 Uiso 1 1 calc R . . C11 C 0.6887(11) 0.5295(6) 0.3306(5) 0.0474(19) Uani 1 1 d . . . H11 H 0.7134 0.5266 0.3895 0.057 Uiso 1 1 calc R . . C12 C 0.7041(10) 0.4431(5) 0.2819(4) 0.0364(16) Uani 1 1 d . . . C13 C 0.9479(9) 0.1822(5) 0.3650(4) 0.0359(16) Uani 1 1 d . . . C14 C 0.8761(10) 0.0942(5) 0.3296(5) 0.0377(17) Uani 1 1 d . . . H14 H 0.8189 0.0905 0.2741 0.045 Uiso 1 1 calc R . . C15 C 0.8961(9) 0.0079(5) 0.3848(5) 0.0372(16) Uani 1 1 d . . . H15 H 0.8572 -0.0586 0.3691 0.045 Uiso 1 1 calc R . . C16 C 0.9790(9) 0.0334(5) 0.4637(4) 0.0316(15) Uani 1 1 d . . . O1 O 0.9755(6) 0.2921(4) 0.2221(3) 0.0381(12) Uani 1 1 d . . . O2 O 0.7471(6) 0.3480(4) 0.3240(3) 0.0378(11) Uani 1 1 d . . . P P 0.9603(3) 0.30703(13) 0.32086(12) 0.0361(5) Uani 1 1 d . . . S S 1.0400(3) 0.16137(12) 0.46884(11) 0.0383(5) Uani 1 1 d . . . Se Se 1.17407(12) 0.39904(6) 0.37478(7) 0.0637(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 0.045(4) 0.032(4) 0.037(4) 0.010(3) -0.005(3) -0.001(3) C2 0.071(5) 0.031(4) 0.044(5) 0.003(4) 0.003(4) -0.006(4) C3 0.086(6) 0.043(5) 0.040(5) -0.004(4) 0.002(4) -0.012(5) C4 0.072(6) 0.069(6) 0.045(5) 0.002(5) -0.009(4) -0.020(5) C5 0.050(4) 0.055(5) 0.046(5) 0.008(4) -0.014(4) 0.008(4) C6 0.044(4) 0.023(3) 0.035(4) 0.006(3) -0.005(3) 0.000(3) C7 0.029(3) 0.030(4) 0.050(4) 0.010(3) -0.003(3) 0.002(3) C8 0.047(4) 0.030(4) 0.063(5) 0.015(4) -0.008(4) 0.006(3) C9 0.051(4) 0.030(4) 0.080(6) 0.025(4) 0.004(4) 0.009(4) C10 0.045(4) 0.027(4) 0.081(7) -0.004(4) 0.011(4) 0.011(3) C11 0.059(5) 0.031(4) 0.052(5) 0.003(4) 0.005(4) 0.007(4) C12 0.042(4) 0.025(4) 0.041(4) 0.010(3) 0.000(3) 0.008(3) C13 0.040(3) 0.019(3) 0.046(4) 0.009(3) -0.008(3) 0.007(3) C14 0.048(4) 0.029(4) 0.034(4) 0.008(3) -0.010(3) 0.000(3) C15 0.044(4) 0.021(3) 0.045(4) 0.000(3) -0.002(3) 0.001(3) C16 0.037(3) 0.023(3) 0.036(4) 0.006(3) 0.006(3) 0.002(3) O1 0.037(2) 0.031(3) 0.044(3) 0.008(2) -0.005(2) 0.004(2) O2 0.045(3) 0.026(2) 0.042(3) 0.011(2) 0.002(2) 0.007(2) P 0.0450(10) 0.0176(9) 0.0428(11) 0.0075(8) -0.0104(8) 0.0023(7) S 0.0564(11) 0.0181(8) 0.0377(11) 0.0034(7) -0.0102(8) 0.0019(8) Se 0.0696(6) 0.0251(5) 0.0878(8) 0.0059(4) -0.0369(5) -0.0070(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 1.369(10) . ? C1 O1 1.405(8) . ? C1 C6 1.410(9) . ? C2 C3 1.366(10) . ? C2 H2 0.9300 . ? C3 C4 1.382(12) . ? C3 H3 0.9300 . ? C4 C5 1.373(12) . ? C4 H4 0.9300 . ? C5 C6 1.377(9) . ? C5 H5 0.9300 . ? C6 C7 1.478(10) . ? C7 C12 1.363(10) . ? C7 C8 1.401(9) . ? C8 C9 1.374(12) . ? C8 H8 0.9300 . ? C9 C10 1.358(11) . ? C9 H9 0.9300 . ? C10 C11 1.382(10) . ? C10 H10 0.9300 . ? C11 C12 1.368(10) . ? C11 H11 0.9300 . ? C12 O2 1.419(8) . ? C13 C14 1.348(9) . ? C13 S 1.725(7) . ? C13 P 1.766(6) . ? C14 C15 1.415(9) . ? C14 H14 0.9300 . ? C15 C16 1.365(9) . ? C15 H15 0.9300 . ? C16 C16 1.444(12) 3_756 ? C16 S 1.714(7) . ? O1 P 1.582(5) . ? O2 P 1.610(5) . ? P Se 2.0502(19) . ? 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 O1 117.2(6) . . ? C2 C1 C6 121.8(7) . . ? O1 C1 C6 120.5(6) . . ? C3 C2 C1 120.3(8) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 119.0(8) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 120.8(8) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 121.5(8) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 116.6(7) . . ? C5 C6 C7 120.9(6) . . ? C1 C6 C7 122.5(6) . . ? C12 C7 C8 116.6(7) . . ? C12 C7 C6 122.8(6) . . ? C8 C7 C6 120.6(7) . . ? C9 C8 C7 121.3(8) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 119.9(7) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.4(7) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 118.7(8) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C7 C12 C11 123.1(7) . . ? C7 C12 O2 118.5(6) . . ? C11 C12 O2 118.3(6) . . ? C14 C13 S 110.7(5) . . ? C14 C13 P 130.0(6) . . ? S C13 P 119.3(4) . . ? C13 C14 C15 113.7(7) . . ? C13 C14 H14 123.1 . . ? C15 C14 H14 123.1 . . ? C16 C15 C14 112.2(6) . . ? C16 C15 H15 123.9 . . ? C14 C15 H15 123.9 . . ? C15 C16 C16 128.1(8) . 3_756 ? C15 C16 S 111.3(5) . . ? C16 C16 S 120.6(7) 3_756 . ? C1 O1 P 125.2(4) . . ? C12 O2 P 115.7(4) . . ? O1 P O2 102.9(3) . . ? O1 P C13 106.7(3) . . ? O2 P C13 102.0(3) . . ? O1 P Se 111.2(2) . . ? O2 P Se 117.2(2) . . ? C13 P Se 115.6(2) . . ? C16 S C13 92.0(3) . . ? 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 -172.1(7) . . . . ? C6 C1 C2 C3 -0.2(11) . . . . ? C1 C2 C3 C4 2.2(12) . . . . ? C2 C3 C4 C5 -2.9(13) . . . . ? C3 C4 C5 C6 1.7(13) . . . . ? C4 C5 C6 C1 0.3(12) . . . . ? C4 C5 C6 C7 179.5(7) . . . . ? C2 C1 C6 C5 -1.1(11) . . . . ? O1 C1 C6 C5 170.6(6) . . . . ? C2 C1 C6 C7 179.8(7) . . . . ? O1 C1 C6 C7 -8.6(10) . . . . ? C5 C6 C7 C12 141.0(7) . . . . ? C1 C6 C7 C12 -39.9(10) . . . . ? C5 C6 C7 C8 -37.9(10) . . . . ? C1 C6 C7 C8 141.2(7) . . . . ? C12 C7 C8 C9 -1.2(11) . . . . ? C6 C7 C8 C9 177.8(7) . . . . ? C7 C8 C9 C10 0.7(12) . . . . ? C8 C9 C10 C11 0.2(12) . . . . ? C9 C10 C11 C12 -0.4(12) . . . . ? C8 C7 C12 C11 1.0(11) . . . . ? C6 C7 C12 C11 -178.0(7) . . . . ? C8 C7 C12 O2 176.9(6) . . . . ? C6 C7 C12 O2 -2.1(10) . . . . ? C10 C11 C12 C7 -0.2(11) . . . . ? C10 C11 C12 O2 -176.1(6) . . . . ? S C13 C14 C15 -0.9(8) . . . . ? P C13 C14 C15 178.5(5) . . . . ? C13 C14 C15 C16 2.0(9) . . . . ? C14 C15 C16 C16 179.5(8) . . . 3_756 ? C14 C15 C16 S -2.3(8) . . . . ? C2 C1 O1 P -123.2(6) . . . . ? C6 C1 O1 P 64.8(8) . . . . ? C7 C12 O2 P 78.7(7) . . . . ? C11 C12 O2 P -105.2(6) . . . . ? C1 O1 P O2 -25.5(6) . . . . ? C1 O1 P C13 81.4(6) . . . . ? C1 O1 P Se -151.8(5) . . . . ? C12 O2 P O1 -61.5(5) . . . . ? C12 O2 P C13 -172.0(5) . . . . ? C12 O2 P Se 60.8(5) . . . . ? C14 C13 P O1 -30.0(8) . . . . ? S C13 P O1 149.3(4) . . . . ? C14 C13 P O2 77.6(8) . . . . ? S C13 P O2 -103.2(4) . . . . ? C14 C13 P Se -154.1(6) . . . . ? S C13 P Se 25.2(5) . . . . ? C15 C16 S C13 1.5(5) . . . . ? C16 C16 S C13 179.9(7) 3_756 . . . ? C14 C13 S C16 -0.4(6) . . . . ? P C13 S C16 -179.8(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.343 _refine_diff_density_min -0.755 _refine_diff_density_rms 0.145 _database_code_depnum_ccdc_archive 'CCDC 833335'