# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 ####################################################################### # # 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_15 _database_code_depnum_ccdc_archive 'CCDC 739448' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H18 O4 Se2' _chemical_formula_sum 'C16 H18 O4 Se2' _chemical_formula_weight 432.22 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41/a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 18.1240(13) _cell_length_b 18.1240(13) _cell_length_c 9.8424(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3233.0(4) _cell_formula_units_Z 8 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 2568 _cell_measurement_theta_min 4.6199 _cell_measurement_theta_max 32.5425 _exptl_crystal_description needle _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.57 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.776 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_absorpt_coefficient_mu 4.589 _exptl_absorpt_correction_T_min 0.40860 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Oxford Diffraction Gemini' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 10.5081 _diffrn_standards_number 2 _diffrn_standards_interval_count 50 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <2% _diffrn_reflns_number 7512 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.1141 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.71 _diffrn_reflns_theta_max 32.56 _reflns_number_total 2642 _reflns_number_gt 1423 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.8 (release 12-01-2007 CrysAlis171 .NET) (compiled Jan 12 2007,17:49:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics WinGX _computing_publication_material WinGX _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^)+(0.0322P)^2^+0.3218P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2642 _refine_ls_number_parameters 101 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0902 _refine_ls_wR_factor_gt 0.0567 _refine_ls_goodness_of_fit_ref 1.157 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.003 _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 Se Se 0.970380(18) 0.693576(17) 0.05585(3) 0.03244(13) Uani 1 1 d . . . O1 O 0.94683(11) 0.54234(11) 0.1192(2) 0.0304(5) Uani 1 1 d . . . O2 O 0.79476(12) 0.50692(13) 0.0737(2) 0.0374(6) Uani 1 1 d . . . H2B H 0.7797 0.5001 0.1513 0.056 Uiso 1 1 calc R . . C1 C 1.02640(16) 0.63707(15) 0.1861(3) 0.0243(6) Uani 1 1 d . . . C2 C 1.08509(19) 0.66287(19) 0.2617(4) 0.0394(8) Uani 1 1 d . . . H2A H 1.1005 0.7116 0.2524 0.047 Uiso 1 1 calc R . . C3 C 1.12114(19) 0.6162(2) 0.3514(4) 0.0415(9) Uani 1 1 d . . . H3A H 1.1608 0.6336 0.4020 0.050 Uiso 1 1 calc R . . C4 C 1.09860(19) 0.5449(2) 0.3658(4) 0.0408(9) Uani 1 1 d . . . H4A H 1.1232 0.5141 0.4262 0.049 Uiso 1 1 calc R . . C5 C 1.03986(18) 0.51766(18) 0.2920(3) 0.0354(8) Uani 1 1 d . . . H5A H 1.0244 0.4692 0.3037 0.042 Uiso 1 1 calc R . . C6 C 1.00430(16) 0.56334(17) 0.2004(3) 0.0256(6) Uani 1 1 d . . . C7 C 0.91880(18) 0.46963(16) 0.1388(4) 0.0333(8) Uani 1 1 d . . . H7A H 0.9039 0.4631 0.2327 0.040 Uiso 1 1 calc R . . H7B H 0.9568 0.4336 0.1183 0.040 Uiso 1 1 calc R . . C8 C 0.85409(18) 0.45851(18) 0.0470(3) 0.0345(8) Uani 1 1 d . . . H8A H 0.8699 0.4653 -0.0463 0.041 Uiso 1 1 calc R . . H8B H 0.8369 0.4081 0.0562 0.041 Uiso 1 1 calc R . . 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 Se 0.0370(2) 0.02248(18) 0.0378(2) 0.00009(15) -0.00752(15) -0.00265(14) O1 0.0310(12) 0.0230(11) 0.0371(12) 0.0036(10) -0.0042(10) -0.0050(10) O2 0.0346(13) 0.0450(14) 0.0325(14) 0.0083(11) 0.0038(11) 0.0009(11) C1 0.0245(15) 0.0215(15) 0.0268(16) 0.0026(13) 0.0009(13) 0.0031(12) C2 0.041(2) 0.0328(18) 0.044(2) -0.0057(17) -0.0037(17) -0.0026(16) C3 0.038(2) 0.040(2) 0.047(2) -0.0085(18) -0.0175(17) 0.0005(17) C4 0.039(2) 0.041(2) 0.042(2) 0.0018(17) -0.0112(17) 0.0099(17) C5 0.0354(18) 0.0268(17) 0.044(2) 0.0048(15) -0.0005(17) 0.0055(14) C6 0.0216(14) 0.0267(15) 0.0284(16) -0.0027(13) 0.0046(13) 0.0019(12) C7 0.0332(18) 0.0213(16) 0.046(2) 0.0014(15) 0.0008(16) -0.0037(14) C8 0.0355(18) 0.0290(17) 0.0389(19) -0.0034(15) 0.0064(15) -0.0053(14) _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 Se C1 1.930(3) . ? Se Se 2.3099(6) 6_664 ? O1 C6 1.367(4) . ? O1 C7 1.425(3) . ? O2 C8 1.413(4) . ? O2 H2B 0.8200 . ? C1 C2 1.379(4) . ? C1 C6 1.402(4) . ? C2 C3 1.387(5) . ? C2 H2A 0.9300 . ? C3 C4 1.362(5) . ? C3 H3A 0.9300 . ? C4 C5 1.380(5) . ? C4 H4A 0.9300 . ? C5 C6 1.383(4) . ? C5 H5A 0.9300 . ? C7 C8 1.494(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? 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 C1 Se Se 103.03(9) . 6_664 ? C6 O1 C7 116.7(2) . . ? C8 O2 H2B 109.5 . . ? C2 C1 C6 119.3(3) . . ? C2 C1 Se 125.7(2) . . ? C6 C1 Se 115.0(2) . . ? C1 C2 C3 120.0(3) . . ? C1 C2 H2A 120.0 . . ? C3 C2 H2A 120.0 . . ? C4 C3 C2 120.2(3) . . ? C4 C3 H3A 119.9 . . ? C2 C3 H3A 119.9 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 H4A 119.5 . . ? C5 C4 H4A 119.5 . . ? C4 C5 C6 119.2(3) . . ? C4 C5 H5A 120.4 . . ? C6 C5 H5A 120.4 . . ? O1 C6 C5 124.7(3) . . ? O1 C6 C1 115.1(3) . . ? C5 C6 C1 120.2(3) . . ? O1 C7 C8 108.8(3) . . ? O1 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? O1 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? O2 C8 C7 113.6(3) . . ? O2 C8 H8A 108.8 . . ? C7 C8 H8A 108.8 . . ? O2 C8 H8B 108.8 . . ? C7 C8 H8B 108.8 . . ? H8A C8 H8B 107.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Se Se C1 C2 2.5(3) 6_664 . . . ? Se Se C1 C6 -176.4(2) 6_664 . . . ? C6 C1 C2 C3 -0.5(5) . . . . ? Se C1 C2 C3 -179.5(3) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C3 C4 C5 C6 1.1(5) . . . . ? C7 O1 C6 C5 4.8(4) . . . . ? C7 O1 C6 C1 -175.0(3) . . . . ? C4 C5 C6 O1 178.3(3) . . . . ? C4 C5 C6 C1 -2.0(5) . . . . ? C2 C1 C6 O1 -178.5(3) . . . . ? Se C1 C6 O1 0.5(3) . . . . ? C2 C1 C6 C5 1.7(5) . . . . ? Se C1 C6 C5 -179.3(2) . . . . ? C6 O1 C7 C8 176.9(3) . . . . ? O1 C7 C8 O2 -62.0(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2B O2 0.82 1.93 2.7207(14) 162.7 8_454 _diffrn_measured_fraction_theta_max 0.899 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.721 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.116 data_22 _database_code_depnum_ccdc_archive 'CCDC 739449' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O6 Se2' _chemical_formula_weight 520.33 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' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.8140(12) _cell_length_b 15.1093(14) _cell_length_c 18.2919(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.682(9) _cell_angle_gamma 90.00 _cell_volume 4361.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5311 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 26.35 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2096 _exptl_absorpt_coefficient_mu 3.423 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.12155 _exptl_absorpt_correction_T_max 0.16904 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 'Stoe IPDS' _diffrn_measurement_method \F-Oscillation _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23241 _diffrn_reflns_av_R_equivalents 0.1160 _diffrn_reflns_av_sigmaI/netI 0.1127 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 26.73 _reflns_number_total 4609 _reflns_number_gt 2475 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Stoe IPDS V2.63' _computing_cell_refinement 'Stoe IPDS V2.63' _computing_data_reduction 'Stoe IPDS V2.63' _computing_structure_solution 'SIR97 (Giacovazzo et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens 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 w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4609 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1194 _refine_ls_R_factor_gt 0.0622 _refine_ls_wR_factor_ref 0.1582 _refine_ls_wR_factor_gt 0.1445 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.41656(5) 0.04119(5) 0.17047(4) 0.0397(2) Uani 1 d . . . Se2 Se 0.37051(5) 0.16151(6) 0.23452(5) 0.0421(2) Uani 1 d . . . O1 O 0.4363(3) -0.0698(3) 0.0490(3) 0.0374(12) Uani 1 d . . . O2 O 0.5091(3) -0.2309(3) 0.1004(3) 0.0488(14) Uani 1 d . . . O3 O 0.6460(4) -0.2223(4) 0.1582(4) 0.0667(18) Uani 1 d . . . O4 O 0.2764(3) 0.2421(3) 0.3435(3) 0.0410(13) Uani 1 d . . . O5 O 0.3752(3) 0.3390(4) 0.4524(3) 0.0491(14) Uani 1 d . . . O6 O 0.4776(4) 0.4255(4) 0.4004(4) 0.0656(18) Uani 1 d . . . C1 C 0.3519(4) 0.0512(5) 0.0778(4) 0.0344(16) Uani 1 d . . . C2 C 0.2888(4) 0.1128(5) 0.0608(5) 0.044(2) Uani 1 d . . . H2 H 0.2755 0.1571 0.0951 0.053 Uiso 1 calc R . . C3 C 0.2453(5) 0.1083(6) -0.0077(5) 0.055(2) Uani 1 d . . . H3 H 0.2011 0.1494 -0.0198 0.066 Uiso 1 calc R . . C4 C 0.2648(5) 0.0467(6) -0.0571(5) 0.054(2) Uani 1 d . . . H4 H 0.2339 0.0448 -0.1033 0.065 Uiso 1 calc R . . C5 C 0.3297(5) -0.0148(5) -0.0415(4) 0.0423(19) Uani 1 d . . . H5 H 0.3434 -0.0573 -0.0771 0.051 Uiso 1 calc R . . C6 C 0.3734(4) -0.0127(5) 0.0261(4) 0.0389(18) Uani 1 d . . . C7 C 0.4589(5) -0.1394(5) 0.0018(5) 0.045(2) Uani 1 d . . . H7A H 0.4734 -0.1151 -0.0461 0.054 Uiso 1 calc R . . H7B H 0.4108 -0.1809 -0.0068 0.054 Uiso 1 calc R . . C8 C 0.5327(5) -0.1861(5) 0.0374(5) 0.046(2) Uani 1 d . . . H8A H 0.5552 -0.2290 0.0026 0.055 Uiso 1 calc R . . H8B H 0.5780 -0.1429 0.0511 0.055 Uiso 1 calc R . . C9 C 0.5769(6) -0.2753(5) 0.1382(6) 0.057(2) Uani 1 d . . . H9A H 0.5560 -0.3024 0.1829 0.068 Uiso 1 calc R . . H9B H 0.5959 -0.3240 0.1069 0.068 Uiso 1 calc R . . C10 C 0.6254(8) -0.1558(7) 0.2098(6) 0.083(3) Uani 1 d . . . H10A H 0.5869 -0.1124 0.1857 0.124 Uiso 1 calc R . . H10B H 0.6773 -0.1260 0.2287 0.124 Uiso 1 calc R . . H10C H 0.5977 -0.1834 0.2505 0.124 Uiso 1 calc R . . C11 C 0.2628(4) 0.1202(5) 0.2651(4) 0.0374(17) Uani 1 d . . . C12 C 0.2194(5) 0.0484(5) 0.2372(4) 0.0404(18) Uani 1 d . . . H12 H 0.2434 0.0133 0.2007 0.048 Uiso 1 calc R . . C13 C 0.1419(5) 0.0260(5) 0.2611(5) 0.046(2) Uani 1 d . . . H13 H 0.1125 -0.0241 0.2410 0.055 Uiso 1 calc R . . C14 C 0.1069(5) 0.0756(5) 0.3138(5) 0.047(2) Uani 1 d . . . H14 H 0.0529 0.0602 0.3299 0.056 Uiso 1 calc R . . C15 C 0.1499(4) 0.1487(5) 0.3440(5) 0.0410(19) Uani 1 d . . . H15 H 0.1262 0.1827 0.3813 0.049 Uiso 1 calc R . . C16 C 0.2276(4) 0.1708(5) 0.3189(4) 0.0362(17) Uani 1 d . . . C17 C 0.2403(5) 0.2994(5) 0.3955(5) 0.045(2) Uani 1 d . . . H17A H 0.2308 0.2673 0.4415 0.054 Uiso 1 calc R . . H17B H 0.1857 0.3241 0.3754 0.054 Uiso 1 calc R . . C18 C 0.3066(5) 0.3728(5) 0.4091(5) 0.047(2) Uani 1 d . . . H18A H 0.3260 0.3940 0.3617 0.057 Uiso 1 calc R . . H18B H 0.2812 0.4233 0.4342 0.057 Uiso 1 calc R . . C19 C 0.4407(6) 0.4032(6) 0.4627(6) 0.062(3) Uani 1 d . . . H19A H 0.4167 0.4573 0.4840 0.074 Uiso 1 calc R . . H19B H 0.4847 0.3800 0.4986 0.074 Uiso 1 calc R . . C20 C 0.5166(6) 0.3520(7) 0.3677(6) 0.067(3) Uani 1 d . . . H20A H 0.5545 0.3222 0.4044 0.101 Uiso 1 calc R . . H20B H 0.5494 0.3727 0.3273 0.101 Uiso 1 calc R . . H20C H 0.4729 0.3105 0.3488 0.101 Uiso 1 calc R . . 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 Se1 0.0282(4) 0.0586(5) 0.0320(4) -0.0075(4) -0.0003(3) 0.0078(4) Se2 0.0283(4) 0.0546(5) 0.0439(5) -0.0132(4) 0.0067(3) -0.0040(3) O1 0.035(3) 0.046(3) 0.032(3) -0.009(2) 0.000(2) 0.005(2) O2 0.049(3) 0.047(3) 0.052(4) 0.002(3) 0.011(3) -0.007(3) O3 0.062(4) 0.062(4) 0.075(5) 0.010(4) -0.001(4) -0.005(3) O4 0.036(3) 0.045(3) 0.043(3) -0.017(3) 0.011(2) 0.000(2) O5 0.044(3) 0.051(3) 0.052(4) 0.002(3) -0.004(3) -0.003(3) O6 0.064(4) 0.056(4) 0.077(5) 0.014(4) 0.003(4) -0.018(3) C1 0.026(3) 0.049(4) 0.028(4) 0.002(3) 0.000(3) -0.003(3) C2 0.028(4) 0.061(5) 0.044(5) 0.000(4) 0.005(3) -0.003(4) C3 0.029(4) 0.075(6) 0.059(6) 0.023(5) -0.007(4) 0.001(4) C4 0.047(5) 0.085(7) 0.031(5) 0.000(5) -0.004(4) -0.020(5) C5 0.046(5) 0.057(5) 0.023(4) -0.003(4) -0.008(3) -0.015(4) C6 0.034(4) 0.056(5) 0.027(4) 0.001(4) 0.004(3) -0.020(3) C7 0.046(5) 0.048(5) 0.044(5) -0.012(4) 0.007(4) -0.012(4) C8 0.049(5) 0.051(5) 0.039(5) -0.007(4) 0.014(4) 0.004(4) C9 0.065(6) 0.038(5) 0.067(7) 0.007(4) 0.003(5) 0.004(4) C10 0.101(9) 0.082(7) 0.063(7) -0.003(6) -0.016(6) 0.002(7) C11 0.025(3) 0.049(4) 0.037(5) 0.007(4) 0.000(3) 0.003(3) C12 0.042(4) 0.051(5) 0.028(4) -0.007(4) 0.004(3) -0.008(4) C13 0.045(5) 0.051(5) 0.043(5) -0.006(4) 0.010(4) -0.015(4) C14 0.028(4) 0.055(5) 0.057(6) 0.012(4) 0.005(4) -0.004(4) C15 0.029(4) 0.049(5) 0.047(5) -0.001(4) 0.013(3) 0.006(3) C16 0.030(3) 0.042(4) 0.036(4) -0.001(3) 0.001(3) 0.006(3) C17 0.032(4) 0.063(5) 0.039(5) 0.000(4) 0.005(3) 0.015(4) C18 0.047(5) 0.043(4) 0.052(6) -0.011(4) 0.001(4) 0.014(4) C19 0.066(6) 0.049(5) 0.069(7) -0.012(5) -0.005(5) -0.013(5) C20 0.061(6) 0.084(7) 0.058(7) 0.023(6) 0.021(5) -0.009(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Se1 C1 1.929(7) . ? Se1 Se2 2.3060(11) . ? Se2 C11 1.930(7) . ? O1 C6 1.361(9) . ? O1 C7 1.422(9) . ? O2 C8 1.408(10) . ? O2 C9 1.409(10) . ? O3 C9 1.385(10) . ? O3 C10 1.431(12) . ? O4 C16 1.384(8) . ? O4 C17 1.432(9) . ? O5 C18 1.399(9) . ? O5 C19 1.422(10) . ? O6 C19 1.356(12) . ? O6 C20 1.422(11) . ? C1 C2 1.386(10) . ? C1 C6 1.408(10) . ? C2 C3 1.391(12) . ? C3 C4 1.347(12) . ? C4 C5 1.400(12) . ? C5 C6 1.378(10) . ? C7 C8 1.479(11) . ? C11 C12 1.365(10) . ? C11 C16 1.390(10) . ? C12 C13 1.370(10) . ? C13 C14 1.366(11) . ? C14 C15 1.392(11) . ? C15 C16 1.380(10) . ? C17 C18 1.535(11) . ? 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 C1 Se1 Se2 102.6(2) . . ? C11 Se2 Se1 101.9(2) . . ? C6 O1 C7 119.3(6) . . ? C8 O2 C9 113.4(6) . . ? C9 O3 C10 111.8(8) . . ? C16 O4 C17 116.7(5) . . ? C18 O5 C19 111.0(6) . . ? C19 O6 C20 112.5(7) . . ? C2 C1 C6 120.8(7) . . ? C2 C1 Se1 125.7(6) . . ? C6 C1 Se1 113.5(5) . . ? C1 C2 C3 118.5(8) . . ? C4 C3 C2 121.1(8) . . ? C3 C4 C5 121.3(8) . . ? C6 C5 C4 119.1(8) . . ? O1 C6 C5 125.2(7) . . ? O1 C6 C1 115.5(6) . . ? C5 C6 C1 119.3(7) . . ? O1 C7 C8 107.9(7) . . ? O2 C8 C7 110.3(7) . . ? O3 C9 O2 114.7(7) . . ? C12 C11 C16 119.1(7) . . ? C12 C11 Se2 125.5(6) . . ? C16 C11 Se2 115.4(6) . . ? C11 C12 C13 121.1(7) . . ? C14 C13 C12 120.0(7) . . ? C13 C14 C15 120.4(7) . . ? C14 C15 C16 118.8(7) . . ? O4 C16 C15 124.7(7) . . ? O4 C16 C11 114.7(6) . . ? C15 C16 C11 120.6(7) . . ? O4 C17 C18 104.3(6) . . ? O5 C18 C17 108.9(6) . . ? O6 C19 O5 114.0(8) . . ? _diffrn_measured_fraction_theta_max 0.479 _diffrn_reflns_theta_full 26.73 _diffrn_measured_fraction_theta_full 0.479 _refine_diff_density_max 2.929 _refine_diff_density_min -0.593 _refine_diff_density_rms 0.131