# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Waro Nakanishi' _publ_contact_author_email NAKANISI@SYS.WAKAYAMA-U.AC.JP _publ_section_title ; How Does Non-covalent Se---Se=O Interaction Stabilize Selenoxides at Naphthalene 1,8-Positions: Structural and Theoretical Investigations ; loop_ _publ_author_name 'Waro Nakanishi' 'Jozef Drabowicz' 'Atsushi Furuta' 'Satoko Hayashi' # Attachment '1LO_rev2.CIF' data_lLO _database_code_depnum_ccdc_archive 'CCDC 688690' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H12 O Se2' _chemical_formula_sum 'C12 H12 O Se2' _chemical_formula_weight 330.14 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 P21/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 5.8460(19) _cell_length_b 14.473(3) _cell_length_c 14.1490(16) _cell_angle_alpha 90.00 _cell_angle_beta 97.660(17) _cell_angle_gamma 90.00 _cell_volume 1186.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 25.5 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.848 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 6.203 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.1475 _exptl_absorpt_correction_T_max 0.3701 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2423 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0490 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2200 _reflns_number_gt 1395 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0230P)^2^+1.5306P] 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 2200 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0773 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.01060(8) 0.52707(4) 0.17972(3) 0.04080(15) Uani 1 1 d . . . O1 O 0.2305(7) 0.5470(3) 0.1202(3) 0.0742(13) Uani 1 1 d . . . C1 C 0.0197(8) 0.6386(3) 0.2615(3) 0.0378(12) Uani 1 1 d . . . C2 C 0.1795(10) 0.6998(4) 0.2394(4) 0.0547(15) Uani 1 1 d . . . H1 H 0.2709 0.6849 0.1926 0.066 Uiso 1 1 calc R . . C3 C 0.2095(12) 0.7853(4) 0.2860(5) 0.0680(19) Uani 1 1 d . . . H2 H 0.3191 0.8270 0.2700 0.082 Uiso 1 1 calc R . . C4 C 0.0769(12) 0.8067(4) 0.3546(4) 0.0640(18) Uani 1 1 d . . . H3 H 0.0954 0.8638 0.3848 0.077 Uiso 1 1 calc R . . C5 C -0.0872(10) 0.7448(4) 0.3811(4) 0.0491(15) Uani 1 1 d . . . C6 C -0.2203(13) 0.7683(4) 0.4541(4) 0.0658(19) Uani 1 1 d . . . H4 H -0.1972 0.8253 0.4842 0.079 Uiso 1 1 calc R . . C7 C -0.3792(12) 0.7104(5) 0.4814(5) 0.076(2) Uani 1 1 d . . . H5 H -0.4665 0.7276 0.5288 0.091 Uiso 1 1 calc R . . C8 C -0.4120(10) 0.6232(4) 0.4370(4) 0.0603(16) Uani 1 1 d . . . H6 H -0.5189 0.5823 0.4568 0.072 Uiso 1 1 calc R . . C9 C -0.2888(9) 0.5975(4) 0.3652(4) 0.0449(13) Uani 1 1 d . . . C10 C -0.1203(9) 0.6569(3) 0.3340(3) 0.0388(12) Uani 1 1 d . . . Se2 Se -0.36772(9) 0.47747(4) 0.31141(4) 0.04933(18) Uani 1 1 d . . . C11 C -0.2467(9) 0.5681(4) 0.0868(3) 0.0520(14) Uani 1 1 d . . . H7 H -0.2807 0.5216 0.0386 0.078 Uiso 1 1 calc R . . H8 H -0.2059 0.6247 0.0578 0.078 Uiso 1 1 calc R . . H9 H -0.3801 0.5782 0.1184 0.078 Uiso 1 1 calc R . . C12 C -0.1261(11) 0.4069(4) 0.3860(4) 0.0717(19) Uani 1 1 d . . . H10 H -0.1387 0.3431 0.3673 0.107 Uiso 1 1 calc R . . H11 H -0.1417 0.4122 0.4524 0.107 Uiso 1 1 calc R . . H12 H 0.0218 0.4303 0.3751 0.107 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 Se1 0.0410(3) 0.0412(3) 0.0412(3) -0.0017(3) 0.0090(2) 0.0047(3) O1 0.051(2) 0.099(4) 0.077(3) -0.002(3) 0.027(2) 0.003(2) C1 0.040(3) 0.037(3) 0.033(3) 0.002(2) -0.007(2) 0.003(2) C2 0.065(4) 0.050(4) 0.049(3) 0.005(3) 0.004(3) -0.005(3) C3 0.089(5) 0.049(4) 0.063(4) 0.007(3) -0.002(4) -0.027(4) C4 0.101(5) 0.038(3) 0.045(4) -0.002(3) -0.018(4) 0.001(4) C5 0.064(4) 0.038(3) 0.039(3) -0.002(2) -0.015(3) 0.003(3) C6 0.093(5) 0.053(4) 0.047(4) -0.018(3) -0.008(4) 0.023(4) C7 0.085(5) 0.085(5) 0.061(4) -0.013(4) 0.020(4) 0.020(4) C8 0.057(4) 0.069(4) 0.056(4) -0.003(3) 0.012(3) 0.005(3) C9 0.045(3) 0.049(3) 0.038(3) 0.001(3) -0.003(2) 0.009(3) C10 0.042(3) 0.039(3) 0.033(3) -0.001(2) -0.006(2) 0.003(2) Se2 0.0500(3) 0.0489(3) 0.0502(3) -0.0015(3) 0.0106(3) -0.0094(3) C11 0.055(4) 0.064(4) 0.036(3) -0.001(3) -0.001(3) -0.010(3) C12 0.092(5) 0.063(4) 0.063(4) 0.018(3) 0.021(4) 0.021(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 Se1 O1 1.653(4) . ? Se1 C11 1.954(5) . ? Se1 C1 1.983(5) . ? Se1 Se2 3.1587(10) . ? C1 C2 1.354(7) . ? C1 C10 1.419(7) . ? C2 C3 1.402(8) . ? C2 H1 0.9300 . ? C3 C4 1.357(8) . ? C3 H2 0.9300 . ? C4 C5 1.399(8) . ? C4 H3 0.9300 . ? C5 C6 1.415(8) . ? C5 C10 1.439(7) . ? C6 C7 1.345(9) . ? C6 H4 0.9300 . ? C7 C8 1.411(8) . ? C7 H5 0.9300 . ? C8 C9 1.372(7) . ? C8 H6 0.9300 . ? C9 C10 1.421(7) . ? C9 Se2 1.928(5) . ? Se2 C12 1.938(6) . ? C11 H7 0.9600 . ? C11 H8 0.9600 . ? C11 H9 0.9600 . ? C12 H10 0.9600 . ? C12 H11 0.9600 . ? C12 H12 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Se1 C11 100.7(2) . . ? O1 Se1 C1 101.1(2) . . ? C11 Se1 C1 96.0(2) . . ? O1 Se1 Se2 173.31(15) . . ? C11 Se1 Se2 85.93(16) . . ? C1 Se1 Se2 78.87(15) . . ? C2 C1 C10 121.8(5) . . ? C2 C1 Se1 111.3(4) . . ? C10 C1 Se1 126.9(4) . . ? C1 C2 C3 121.0(6) . . ? C1 C2 H1 119.5 . . ? C3 C2 H1 119.5 . . ? C4 C3 C2 119.4(6) . . ? C4 C3 H2 120.3 . . ? C2 C3 H2 120.3 . . ? C3 C4 C5 121.6(6) . . ? C3 C4 H3 119.2 . . ? C5 C4 H3 119.2 . . ? C4 C5 C6 120.4(6) . . ? C4 C5 C10 119.8(6) . . ? C6 C5 C10 119.8(6) . . ? C7 C6 C5 121.9(6) . . ? C7 C6 H4 119.1 . . ? C5 C6 H4 119.1 . . ? C6 C7 C8 119.2(6) . . ? C6 C7 H5 120.4 . . ? C8 C7 H5 120.4 . . ? C9 C8 C7 121.1(6) . . ? C9 C8 H6 119.4 . . ? C7 C8 H6 119.4 . . ? C8 C9 C10 121.4(5) . . ? C8 C9 Se2 114.5(4) . . ? C10 C9 Se2 124.1(4) . . ? C1 C10 C9 127.0(4) . . ? C1 C10 C5 116.4(5) . . ? C9 C10 C5 116.5(5) . . ? C9 Se2 C12 98.1(2) . . ? C9 Se2 Se1 83.03(16) . . ? C12 Se2 Se1 85.65(18) . . ? Se1 C11 H7 109.5 . . ? Se1 C11 H8 109.5 . . ? H7 C11 H8 109.5 . . ? Se1 C11 H9 109.5 . . ? H7 C11 H9 109.5 . . ? H8 C11 H9 109.5 . . ? Se2 C12 H10 109.5 . . ? Se2 C12 H11 109.5 . . ? H10 C12 H11 109.5 . . ? Se2 C12 H12 109.5 . . ? H10 C12 H12 109.5 . . ? H11 C12 H12 109.5 . . ? 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 Se1 C1 C2 5.9(4) . . . . ? C11 Se1 C1 C2 -96.3(4) . . . . ? Se2 Se1 C1 C2 179.1(4) . . . . ? O1 Se1 C1 C10 -175.0(4) . . . . ? C11 Se1 C1 C10 82.8(4) . . . . ? Se2 Se1 C1 C10 -1.8(4) . . . . ? C10 C1 C2 C3 -1.6(8) . . . . ? Se1 C1 C2 C3 177.6(4) . . . . ? C1 C2 C3 C4 0.4(9) . . . . ? C2 C3 C4 C5 0.9(9) . . . . ? C3 C4 C5 C6 178.9(6) . . . . ? C3 C4 C5 C10 -1.0(9) . . . . ? C4 C5 C6 C7 -180.0(6) . . . . ? C10 C5 C6 C7 -0.1(9) . . . . ? C5 C6 C7 C8 1.0(10) . . . . ? C6 C7 C8 C9 -1.7(10) . . . . ? C7 C8 C9 C10 1.3(8) . . . . ? C7 C8 C9 Se2 -177.9(5) . . . . ? C2 C1 C10 C9 -178.3(5) . . . . ? Se1 C1 C10 C9 2.7(7) . . . . ? C2 C1 C10 C5 1.4(7) . . . . ? Se1 C1 C10 C5 -177.6(4) . . . . ? C8 C9 C10 C1 179.4(5) . . . . ? Se2 C9 C10 C1 -1.5(7) . . . . ? C8 C9 C10 C5 -0.3(7) . . . . ? Se2 C9 C10 C5 178.8(4) . . . . ? C4 C5 C10 C1 -0.1(7) . . . . ? C6 C5 C10 C1 180.0(5) . . . . ? C4 C5 C10 C9 179.6(5) . . . . ? C6 C5 C10 C9 -0.3(7) . . . . ? C8 C9 Se2 C12 -96.2(4) . . . . ? C10 C9 Se2 C12 84.6(4) . . . . ? C8 C9 Se2 Se1 179.2(4) . . . . ? C10 C9 Se2 Se1 0.1(4) . . . . ? O1 Se1 Se2 C9 91.6(13) . . . . ? C11 Se1 Se2 C9 -96.1(2) . . . . ? C1 Se1 Se2 C9 0.8(2) . . . . ? O1 Se1 Se2 C12 -7.2(14) . . . . ? C11 Se1 Se2 C12 165.1(2) . . . . ? C1 Se1 Se2 C12 -98.0(2) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.723 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.083 # Attachment '1OO_rev2.CIF' data_1OO _database_code_depnum_ccdc_archive 'CCDC 688691' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C12 H12 O2 Se2), 5(H2 O)' _chemical_formula_sum 'C12 H17 O4.50 Se2' _chemical_formula_weight 391.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 _symmetry_space_group_name_Hall ' -C 2yc' _symmetry_Int_Tables_number 15 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 25.549(9) _cell_length_b 5.8653(18) _cell_length_c 20.850(8) _cell_angle_alpha 90.00 _cell_angle_beta 117.329(4) _cell_angle_gamma 90.00 _cell_volume 2775.6(16) _cell_formula_units_Z 8 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.24 _cell_measurement_theta_max 24.99 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.872 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 5.336 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1975 _exptl_absorpt_correction_T_max 0.3489 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 103(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 7.31 _diffrn_reflns_number 10693 _diffrn_reflns_av_R_equivalents 0.0384 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.24 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2435 _reflns_number_gt 2333 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'Crystal Clear' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics yadokari-XG _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0287P)^2^+0.3206P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2435 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0536 _refine_ls_wR_factor_gt 0.0529 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.575181(9) -0.02525(4) 0.080592(11) 0.00833(9) Uani 1 1 d . . . O1 O 0.56690(6) -0.2835(2) 0.10925(8) 0.0129(3) Uani 1 1 d . . . C1 C 0.66078(9) -0.0019(3) 0.11842(12) 0.0097(5) Uani 1 1 d . . . C2 C 0.69123(9) -0.1705(4) 0.16667(12) 0.0132(5) Uani 1 1 d . . . H1 H 0.6702 -0.2834 0.1782 0.016 Uiso 1 1 calc R . . C3 C 0.75303(9) -0.1790(4) 0.19931(12) 0.0167(5) Uani 1 1 d . . . H2 H 0.7737 -0.2972 0.2325 0.020 Uiso 1 1 calc R . . C4 C 0.78334(10) -0.0161(4) 0.18301(13) 0.0156(5) Uani 1 1 d . . . H3 H 0.8252 -0.0214 0.2053 0.019 Uiso 1 1 calc R . . C5 C 0.75315(9) 0.1606(4) 0.13334(12) 0.0124(5) Uani 1 1 d . . . C6 C 0.78650(10) 0.3283(4) 0.11841(13) 0.0166(5) Uani 1 1 d . . . H4 H 0.8283 0.3205 0.1422 0.020 Uiso 1 1 calc R . . C7 C 0.75918(11) 0.4993(4) 0.07051(14) 0.0204(6) Uani 1 1 d . . . H5 H 0.7818 0.6091 0.0606 0.024 Uiso 1 1 calc R . . C8 C 0.69749(10) 0.5132(4) 0.03581(13) 0.0165(5) Uani 1 1 d . . . H6 H 0.6786 0.6329 0.0024 0.020 Uiso 1 1 calc R . . C9 C 0.66385(9) 0.3561(4) 0.04946(12) 0.0111(5) Uani 1 1 d . . . C10 C 0.68980(9) 0.1724(4) 0.09855(11) 0.0102(5) Uani 1 1 d . . . Se2 Se 0.578463(9) 0.40908(3) -0.006452(11) 0.00892(9) Uani 1 1 d . . . O2 O 0.57594(7) 0.6703(2) -0.04057(8) 0.0152(4) Uani 1 1 d . . . C11 C 0.57186(10) 0.1774(4) 0.15215(12) 0.0139(5) Uani 1 1 d . . . H7 H 0.5309 0.1922 0.1436 0.021 Uiso 1 1 calc R . . H8 H 0.5871 0.3277 0.1485 0.021 Uiso 1 1 calc R . . H9 H 0.5959 0.1147 0.2005 0.021 Uiso 1 1 calc R . . C12 C 0.57104(10) 0.2136(4) -0.08491(12) 0.0132(5) Uani 1 1 d . . . H10 H 0.5320 0.2345 -0.1262 0.020 Uiso 1 1 calc R . . H11 H 0.5758 0.0542 -0.0692 0.020 Uiso 1 1 calc R . . H12 H 0.6015 0.2531 -0.0992 0.020 Uiso 1 1 calc R . . O3 O 0.57237(8) 0.6480(3) 0.24519(10) 0.0182(4) Uani 1 1 d . . . H13 H 0.5718(13) 0.667(5) 0.1978(18) 0.048(9) Uiso 1 1 d . . . H14 H 0.5534(12) 0.740(5) 0.2470(14) 0.021(8) Uiso 1 1 d . . . O4 O 0.58967(8) 0.2688(3) 0.33588(10) 0.0190(4) Uani 1 1 d . . . H15 H 0.5848(11) 0.299(5) 0.3715(16) 0.026(8) Uiso 1 1 d . . . H16 H 0.5812(12) 0.394(6) 0.3053(16) 0.041(9) Uiso 1 1 d . . . O5 O 0.5000 -0.0074(4) 0.2500 0.0148(5) Uani 1 2 d S . . H17 H 0.4701(11) 0.078(5) 0.2173(15) 0.033(8) Uiso 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 Se1 0.00878(14) 0.00718(13) 0.01024(15) 0.00059(8) 0.00539(11) -0.00084(8) O1 0.0183(9) 0.0068(8) 0.0175(9) 0.0028(6) 0.0117(7) -0.0023(6) C1 0.0094(11) 0.0103(11) 0.0107(12) -0.0034(9) 0.0057(10) -0.0016(8) C2 0.0136(12) 0.0121(11) 0.0148(13) -0.0005(9) 0.0072(10) -0.0003(9) C3 0.0158(13) 0.0158(12) 0.0161(13) 0.0022(10) 0.0051(11) 0.0057(9) C4 0.0083(12) 0.0224(13) 0.0147(13) -0.0018(10) 0.0040(10) 0.0029(9) C5 0.0109(11) 0.0181(12) 0.0108(12) -0.0045(9) 0.0072(10) -0.0011(9) C6 0.0105(11) 0.0243(13) 0.0172(13) -0.0053(11) 0.0083(10) -0.0041(10) C7 0.0210(14) 0.0229(14) 0.0237(15) -0.0014(10) 0.0158(12) -0.0101(10) C8 0.0193(13) 0.0162(12) 0.0152(13) 0.0014(10) 0.0091(11) -0.0033(9) C9 0.0087(11) 0.0133(11) 0.0116(12) -0.0025(9) 0.0050(9) -0.0011(8) C10 0.0127(11) 0.0106(11) 0.0093(12) -0.0049(9) 0.0068(10) -0.0022(8) Se2 0.01173(14) 0.00713(14) 0.00960(15) 0.00083(8) 0.00636(11) 0.00047(8) O2 0.0242(9) 0.0060(8) 0.0192(9) 0.0046(7) 0.0133(8) 0.0021(6) C11 0.0177(12) 0.0099(11) 0.0187(13) -0.0023(10) 0.0121(11) -0.0006(9) C12 0.0155(12) 0.0131(12) 0.0128(12) -0.0016(9) 0.0080(10) -0.0008(9) O3 0.0206(9) 0.0193(10) 0.0190(10) 0.0043(8) 0.0128(8) 0.0089(8) O4 0.0286(10) 0.0159(9) 0.0190(10) -0.0016(8) 0.0163(9) -0.0004(7) O5 0.0184(13) 0.0121(12) 0.0153(13) 0.000 0.0089(11) 0.000 _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 O1 1.6771(15) . ? Se1 C11 1.940(2) . ? Se1 C1 1.959(2) . ? Se1 Se2 3.1512(8) . ? C1 C2 1.370(3) . ? C1 C10 1.431(3) . ? C2 C3 1.404(3) . ? C2 H1 0.9500 . ? C3 C4 1.367(3) . ? C3 H2 0.9500 . ? C4 C5 1.417(3) . ? C4 H3 0.9500 . ? C5 C6 1.426(3) . ? C5 C10 1.440(3) . ? C6 C7 1.361(3) . ? C6 H4 0.9500 . ? C7 C8 1.403(3) . ? C7 H5 0.9500 . ? C8 C9 1.376(3) . ? C8 H6 0.9500 . ? C9 C10 1.423(3) . ? C9 Se2 1.970(2) . ? Se2 O2 1.6780(15) . ? Se2 C12 1.934(2) . ? C11 H7 0.9800 . ? C11 H8 0.9800 . ? C11 H9 0.9800 . ? C12 H10 0.9800 . ? C12 H11 0.9800 . ? C12 H12 0.9800 . ? O3 H13 0.99(3) . ? O3 H14 0.74(3) . ? O4 H15 0.83(3) . ? O4 H16 0.93(3) . ? O5 H17 0.91(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 O1 Se1 C11 102.85(9) . . ? O1 Se1 C1 102.69(8) . . ? C11 Se1 C1 94.73(9) . . ? O1 Se1 Se2 167.54(5) . . ? C11 Se1 Se2 88.26(7) . . ? C1 Se1 Se2 81.69(6) . . ? C2 C1 C10 122.2(2) . . ? C2 C1 Se1 113.45(16) . . ? C10 C1 Se1 124.33(16) . . ? C1 C2 C3 121.0(2) . . ? C1 C2 H1 119.5 . . ? C3 C2 H1 119.5 . . ? C4 C3 C2 119.6(2) . . ? C4 C3 H2 120.2 . . ? C2 C3 H2 120.2 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H3 119.6 . . ? C5 C4 H3 119.6 . . ? C4 C5 C6 119.0(2) . . ? C4 C5 C10 120.8(2) . . ? C6 C5 C10 120.2(2) . . ? C7 C6 C5 120.8(2) . . ? C7 C6 H4 119.6 . . ? C5 C6 H4 119.6 . . ? C6 C7 C8 119.8(2) . . ? C6 C7 H5 120.1 . . ? C8 C7 H5 120.1 . . ? C9 C8 C7 121.0(2) . . ? C9 C8 H6 119.5 . . ? C7 C8 H6 119.5 . . ? C8 C9 C10 121.8(2) . . ? C8 C9 Se2 113.53(17) . . ? C10 C9 Se2 124.67(16) . . ? C9 C10 C1 128.1(2) . . ? C9 C10 C5 116.34(19) . . ? C1 C10 C5 115.57(19) . . ? O2 Se2 C12 102.29(9) . . ? O2 Se2 C9 102.21(8) . . ? C12 Se2 C9 93.38(9) . . ? O2 Se2 Se1 167.51(5) . . ? C12 Se2 Se1 89.41(7) . . ? C9 Se2 Se1 81.18(7) . . ? Se1 C11 H7 109.5 . . ? Se1 C11 H8 109.5 . . ? H7 C11 H8 109.5 . . ? Se1 C11 H9 109.5 . . ? H7 C11 H9 109.5 . . ? H8 C11 H9 109.5 . . ? Se2 C12 H10 109.5 . . ? Se2 C12 H11 109.5 . . ? H10 C12 H11 109.5 . . ? Se2 C12 H12 109.5 . . ? H10 C12 H12 109.5 . . ? H11 C12 H12 109.5 . . ? H13 O3 H14 105(3) . . ? H15 O4 H16 111(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 Se1 C1 C2 -10.85(18) . . . . ? C11 Se1 C1 C2 93.47(17) . . . . ? Se2 Se1 C1 C2 -178.99(17) . . . . ? O1 Se1 C1 C10 169.19(17) . . . . ? C11 Se1 C1 C10 -86.49(19) . . . . ? Se2 Se1 C1 C10 1.06(17) . . . . ? C10 C1 C2 C3 0.2(3) . . . . ? Se1 C1 C2 C3 -179.72(17) . . . . ? C1 C2 C3 C4 0.3(3) . . . . ? C2 C3 C4 C5 -0.3(3) . . . . ? C3 C4 C5 C6 179.4(2) . . . . ? C3 C4 C5 C10 -0.3(3) . . . . ? C4 C5 C6 C7 179.3(2) . . . . ? C10 C5 C6 C7 -1.0(3) . . . . ? C5 C6 C7 C8 0.7(4) . . . . ? C6 C7 C8 C9 0.1(4) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C7 C8 C9 Se2 -179.35(18) . . . . ? C8 C9 C10 C1 179.6(2) . . . . ? Se2 C9 C10 C1 -1.8(3) . . . . ? C8 C9 C10 C5 0.2(3) . . . . ? Se2 C9 C10 C5 178.90(15) . . . . ? C2 C1 C10 C9 179.9(2) . . . . ? Se1 C1 C10 C9 -0.1(3) . . . . ? C2 C1 C10 C5 -0.8(3) . . . . ? Se1 C1 C10 C5 179.19(15) . . . . ? C4 C5 C10 C9 -179.8(2) . . . . ? C6 C5 C10 C9 0.5(3) . . . . ? C4 C5 C10 C1 0.8(3) . . . . ? C6 C5 C10 C1 -178.9(2) . . . . ? C8 C9 Se2 O2 -11.70(18) . . . . ? C10 C9 Se2 O2 169.54(18) . . . . ? C8 C9 Se2 C12 91.66(18) . . . . ? C10 C9 Se2 C12 -87.10(19) . . . . ? C8 C9 Se2 Se1 -179.47(17) . . . . ? C10 C9 Se2 Se1 1.78(17) . . . . ? O1 Se1 Se2 O2 140.3(3) . . . . ? C11 Se1 Se2 O2 -13.1(3) . . . . ? C1 Se1 Se2 O2 -108.1(3) . . . . ? O1 Se1 Se2 C12 -19.4(2) . . . . ? C11 Se1 Se2 C12 -172.75(9) . . . . ? C1 Se1 Se2 C12 92.21(9) . . . . ? O1 Se1 Se2 C9 -112.9(2) . . . . ? C11 Se1 Se2 C9 93.74(9) . . . . ? C1 Se1 Se2 C9 -1.30(9) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.443 _refine_diff_density_min -0.667 _refine_diff_density_rms 0.094