# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge ? loop_ _publ_author_name 'Sine Larsen' 'Lars Henriksen' 'Jette Oddershede' _publ_contact_author_name 'Prof Sine Larsen' _publ_contact_author_address ; Centre for Crystallographic Studies Department of Chemistry University of Copenhagen Universitetsparken 5 DK-2100 Copenhagen DK-2100 DENMARK ; _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_contact_author_email sine@ccs.ki.ku.dk _publ_section_title ; Relations between 77Se NMR chemical shifts of (phenylseleno)benzenes and their molecular structures derived from nine X-ray crystal structures ; data_1 _database_code_CSD 197542 _chemical_name_systematic ; 4,6-bis(phenylseleno)-3-methoxyphenol ; _chemical_name_common 1 _chemical_formula_moiety 'C19 H16 O2 Se2' _chemical_formula_sum 'C19 H16 O2 Se2' _chemical_formula_weight 434.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.516(4) _cell_length_b 18.569(6) _cell_length_c 8.832(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.21(4) _cell_angle_gamma 90.00 _cell_volume 1697.5(12) _cell_formula_units_Z 4 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 40.20 _cell_measurement_theta_max 42.22 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.699 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 5.497 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.029 _exptl_absorpt_correction_T_max 0.214 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type Cu-Ka _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 1.3 _diffrn_reflns_number 7508 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0123 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.27 _diffrn_reflns_theta_max 74.90 _reflns_number_total 3478 _reflns_number_gt 3288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0407P)^2^+1.6682P] 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 SHELXL _refine_ls_extinction_coef 0.00274(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3478 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0307 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _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 0.38324(3) 0.520544(19) 0.17392(3) 0.04727(12) Uani 1 1 d . . . Se2 Se 0.84404(2) 0.627419(19) 0.56597(3) 0.04416(12) Uani 1 1 d . . . C1 C 0.4648(2) 0.57163(16) 0.3530(3) 0.0413(6) Uani 1 1 d . . . C2 C 0.3938(2) 0.59253(17) 0.4647(3) 0.0429(6) Uani 1 1 d . . . C3 C 0.4547(2) 0.62600(16) 0.5999(3) 0.0422(6) Uani 1 1 d . . . H3 H 0.4055 0.6412 0.6745 0.051 Uiso 1 1 calc R . . C4 C 0.5870(2) 0.63688(15) 0.6249(3) 0.0387(6) Uani 1 1 d . . . C5 C 0.6606(2) 0.61438(15) 0.5150(3) 0.0380(6) Uani 1 1 d . . . C6 C 0.5982(2) 0.58233(16) 0.3806(3) 0.0398(6) Uani 1 1 d . . . H6 H 0.6472 0.5673 0.3056 0.048 Uiso 1 1 calc R . . C11 C 0.3076(2) 0.59839(19) 0.0443(3) 0.0466(7) Uani 1 1 d . . . C21 C 0.8872(2) 0.61939(16) 0.3632(3) 0.0384(6) Uani 1 1 d . . . O2 O 0.26344(17) 0.58308(14) 0.4495(2) 0.0539(6) Uani 1 1 d . . . H2 H 0.2372 0.5572 0.3722 0.081 Uiso 1 1 calc R . . O4 O 0.65498(16) 0.66849(12) 0.75417(19) 0.0437(5) Uani 1 1 d . . . C7 C 0.5832(3) 0.6910(2) 0.8706(3) 0.0545(8) Uani 1 1 d . . . H71 H 0.5392 0.6494 0.9058 0.065 Uiso 1 1 calc R . . H72 H 0.5190 0.7272 0.8274 0.065 Uiso 1 1 calc R . . H73 H 0.6425 0.7119 0.9577 0.065 Uiso 1 1 calc R . . C12 C 0.3014(3) 0.6693(2) 0.0921(3) 0.0519(8) Uani 1 1 d . . . H12 H 0.3404 0.6828 0.1934 0.062 Uiso 1 1 calc R . . C13 C 0.2379(3) 0.7205(2) -0.0086(3) 0.0559(8) Uani 1 1 d . . . H13 H 0.2344 0.7691 0.0243 0.067 Uiso 1 1 calc R . . C14 C 0.1793(3) 0.7014(2) -0.1574(3) 0.0578(9) Uani 1 1 d . . . H14 H 0.1349 0.7364 -0.2254 0.069 Uiso 1 1 calc R . . C15 C 0.1869(3) 0.6308(2) -0.2045(3) 0.0575(9) Uani 1 1 d . . . H15 H 0.1475 0.6174 -0.3059 0.069 Uiso 1 1 calc R . . C16 C 0.2509(2) 0.5794(2) -0.1064(3) 0.0516(8) Uani 1 1 d . . . H16 H 0.2565 0.5312 -0.1408 0.062 Uiso 1 1 calc R . . C22 C 0.8691(3) 0.6767(2) 0.2624(3) 0.0542(7) Uani 1 1 d . . . H22 H 0.8292 0.7195 0.2898 0.065 Uiso 1 1 calc R . . C23 C 0.9090(4) 0.6720(2) 0.1204(4) 0.0612(8) Uani 1 1 d . . . H23 H 0.8957 0.7115 0.0511 0.073 Uiso 1 1 calc R . . C24 C 0.9674(3) 0.61061(19) 0.0803(3) 0.0508(7) Uani 1 1 d . . . H24 H 0.9942 0.6075 -0.0167 0.061 Uiso 1 1 calc R . . C25 C 0.9868(3) 0.5541(2) 0.1802(4) 0.0578(8) Uani 1 1 d . . . H25 H 1.0285 0.5119 0.1530 0.069 Uiso 1 1 calc R . . C26 C 0.9461(3) 0.55773(19) 0.3222(3) 0.0528(7) Uani 1 1 d . . . H26 H 0.9589 0.5178 0.3904 0.063 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 0.03401(16) 0.0810(2) 0.02664(16) -0.02316(13) 0.00482(11) -0.01109(13) Se2 0.02477(15) 0.0827(2) 0.02560(16) -0.01529(12) 0.00621(10) -0.01266(12) C1 0.0299(11) 0.0709(17) 0.0238(11) -0.0152(11) 0.0068(9) -0.0090(11) C2 0.0257(11) 0.0763(19) 0.0280(12) -0.0161(12) 0.0084(9) -0.0118(11) C3 0.0293(12) 0.0744(18) 0.0250(12) -0.0183(11) 0.0106(9) -0.0113(11) C4 0.0299(11) 0.0660(16) 0.0212(11) -0.0146(11) 0.0075(9) -0.0114(11) C5 0.0251(11) 0.0652(16) 0.0248(11) -0.0112(11) 0.0078(9) -0.0090(10) C6 0.0288(11) 0.0684(17) 0.0238(11) -0.0151(11) 0.0089(9) -0.0077(11) C11 0.0267(11) 0.093(2) 0.0215(11) -0.0169(13) 0.0084(9) -0.0161(13) C21 0.0196(10) 0.0696(17) 0.0267(12) -0.0131(11) 0.0059(8) -0.0093(10) O2 0.0260(8) 0.1019(17) 0.0353(10) -0.0293(10) 0.0097(7) -0.0171(9) O4 0.0302(8) 0.0786(13) 0.0241(8) -0.0210(8) 0.0094(7) -0.0162(8) C7 0.0396(14) 0.097(2) 0.0302(13) -0.0314(14) 0.0143(11) -0.0189(15) C12 0.0435(14) 0.091(2) 0.0219(12) -0.0122(13) 0.0067(10) -0.0169(15) C13 0.0488(16) 0.090(2) 0.0302(14) -0.0040(14) 0.0122(12) -0.0133(16) C14 0.0357(14) 0.115(3) 0.0252(13) 0.0001(15) 0.0111(10) -0.0094(16) C15 0.0255(12) 0.126(3) 0.0222(12) -0.0162(15) 0.0075(10) -0.0141(15) C16 0.0245(11) 0.106(2) 0.0259(12) -0.0247(14) 0.0089(9) -0.0133(13) C22 0.0523(17) 0.076(2) 0.0372(15) -0.0043(14) 0.0154(12) 0.0106(15) C23 0.066(2) 0.082(2) 0.0391(16) -0.0009(15) 0.0199(14) -0.0009(17) C24 0.0337(13) 0.087(2) 0.0354(14) -0.0176(14) 0.0170(11) -0.0164(13) C25 0.0508(17) 0.084(2) 0.0396(16) -0.0246(16) 0.0112(13) 0.0059(16) C26 0.0573(17) 0.0680(19) 0.0330(14) -0.0133(13) 0.0079(12) -0.0012(15) _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 1.912(2) . ? Se1 C11 1.926(3) . ? Se2 C5 1.917(2) . ? Se2 C21 1.930(3) . ? C1 C2 1.394(3) . ? C1 C6 1.395(3) . ? C2 O2 1.365(3) . ? C2 C3 1.397(3) . ? C3 C4 1.384(3) . ? C3 H3 0.9500 . ? C4 O4 1.367(3) . ? C4 C5 1.408(3) . ? C5 C6 1.385(3) . ? C6 H6 0.9500 . ? C11 C12 1.388(5) . ? C11 C16 1.403(3) . ? C21 C22 1.379(4) . ? C21 C26 1.380(4) . ? O2 H2 0.8400 . ? O4 C7 1.442(3) . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C12 C13 1.389(5) . ? C12 H12 0.9500 . ? C13 C14 1.395(4) . ? C13 H13 0.9500 . ? C14 C15 1.382(5) . ? C14 H14 0.9500 . ? C15 C16 1.382(5) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C22 C23 1.395(4) . ? C22 H22 0.9500 . ? C23 C24 1.370(5) . ? C23 H23 0.9500 . ? C24 C25 1.363(5) . ? C24 H24 0.9500 . ? C25 C26 1.397(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C11 101.36(13) . . ? C5 Se2 C21 99.50(10) . . ? C2 C1 C6 119.0(2) . . ? C2 C1 Se1 120.38(18) . . ? C6 C1 Se1 120.31(18) . . ? O2 C2 C1 123.3(2) . . ? O2 C2 C3 116.2(2) . . ? C1 C2 C3 120.5(2) . . ? C4 C3 C2 119.8(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? O4 C4 C3 123.9(2) . . ? O4 C4 C5 115.7(2) . . ? C3 C4 C5 120.4(2) . . ? C6 C5 C4 119.0(2) . . ? C6 C5 Se2 124.01(18) . . ? C4 C5 Se2 117.00(17) . . ? C5 C6 C1 121.3(2) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C12 C11 C16 119.5(3) . . ? C12 C11 Se1 124.6(2) . . ? C16 C11 Se1 115.8(3) . . ? C22 C21 C26 119.2(2) . . ? C22 C21 Se2 120.8(2) . . ? C26 C21 Se2 119.9(2) . . ? C2 O2 H2 109.5 . . ? C4 O4 C7 117.22(19) . . ? O4 C7 H71 109.5 . . ? O4 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? O4 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C13 C14 120.7(4) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 120.9(3) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C15 C16 C11 119.9(3) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.7(3) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.7(3) . . ? C24 C25 H25 119.7 . . ? C26 C25 H25 119.7 . . ? C21 C26 C25 119.9(3) . . ? C21 C26 H26 120.0 . . ? C25 C26 H26 120.0 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 74.90 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.500 _refine_diff_density_min -0.980 _refine_diff_density_rms 0.069 #===END data_2 _database_code_CSD 197543 _chemical_name_systematic ; 2,3-dimethyl-4-(phenylseleno)phenol ; _chemical_name_common 2 _chemical_formula_moiety 'C14 H14 O Se' _chemical_formula_sum 'C14 H14 O Se' _chemical_formula_weight 277.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2242(15) _cell_length_b 7.9556(11) _cell_length_c 11.007(2) _cell_angle_alpha 83.594(14) _cell_angle_beta 73.236(16) _cell_angle_gamma 86.000(14) _cell_volume 601.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 39.52 _cell_measurement_theta_max 42.57 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.531 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 4.014 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.030 _exptl_absorpt_correction_T_max 0.199 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 2.0 _diffrn_reflns_number 4817 _diffrn_reflns_av_R_equivalents 0.0489 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 74.85 _reflns_number_total 2454 _reflns_number_gt 2419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0275P)^2^+0.4290P] 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 2454 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0250 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0678 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.001 _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 0.17393(2) 0.25609(2) 0.121822(16) 0.01567(8) Uani 1 1 d . . . C1 C 0.2772(3) 0.4657(2) 0.13830(17) 0.0153(3) Uani 1 1 d . . . C2 C 0.4230(3) 0.4737(2) 0.19842(17) 0.0152(4) Uani 1 1 d . . . C3 C 0.4998(3) 0.6321(3) 0.19728(17) 0.0159(4) Uani 1 1 d . . . C4 C 0.4259(3) 0.7762(3) 0.14002(17) 0.0171(4) Uani 1 1 d . . . C5 C 0.2808(3) 0.7663(3) 0.08090(18) 0.0184(4) Uani 1 1 d . . . H5 H 0.2325 0.8656 0.0418 0.022 Uiso 1 1 calc R . . C6 C 0.2080(3) 0.6111(3) 0.07968(17) 0.0181(4) Uani 1 1 d . . . H6 H 0.1102 0.6032 0.0387 0.022 Uiso 1 1 calc R . . O4 O 0.5028(2) 0.92766(18) 0.14359(14) 0.0219(3) Uani 1 1 d . . . H4 H 0.4329 1.0074 0.1219 0.033 Uiso 1 1 calc R . . C11 C 0.0013(3) 0.2070(3) 0.29029(17) 0.0160(3) Uani 1 1 d . . . C12 C -0.0869(3) 0.0520(3) 0.31484(19) 0.0211(4) Uani 1 1 d . . . H12 H -0.0579 -0.0250 0.2512 0.025 Uiso 1 1 calc R . . C13 C -0.2174(3) 0.0103(3) 0.4330(2) 0.0240(4) Uani 1 1 d . . . H13 H -0.2782 -0.0953 0.4499 0.029 Uiso 1 1 calc R . . C14 C -0.2595(3) 0.1217(3) 0.52623(19) 0.0238(4) Uani 1 1 d . . . H14 H -0.3485 0.0926 0.6070 0.029 Uiso 1 1 calc R . . C15 C -0.1708(3) 0.2759(3) 0.5010(2) 0.0257(4) Uani 1 1 d . . . H15 H -0.1996 0.3525 0.5648 0.031 Uiso 1 1 calc R . . C16 C -0.0398(3) 0.3195(3) 0.38266(19) 0.0207(4) Uani 1 1 d . . . H16 H 0.0206 0.4253 0.3657 0.025 Uiso 1 1 calc R . . C7 C 0.4968(3) 0.3197(3) 0.26487(19) 0.0211(4) Uani 1 1 d . . . H71 H 0.4107 0.2262 0.2743 0.025 Uiso 1 1 calc R . . H72 H 0.5004 0.3449 0.3493 0.025 Uiso 1 1 calc R . . H73 H 0.6274 0.2873 0.2144 0.025 Uiso 1 1 calc R . . C8 C 0.6620(3) 0.6465(3) 0.2564(2) 0.0237(4) Uani 1 1 d . . . H81 H 0.7684 0.5666 0.2213 0.028 Uiso 1 1 calc R . . H82 H 0.6143 0.6202 0.3490 0.028 Uiso 1 1 calc R . . H83 H 0.7083 0.7620 0.2373 0.028 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 0.01889(12) 0.01264(13) 0.01509(11) -0.00185(8) -0.00351(8) -0.00279(8) C1 0.0170(8) 0.0110(8) 0.0154(8) -0.0015(7) -0.0007(6) -0.0006(7) C2 0.0160(8) 0.0117(9) 0.0156(8) -0.0014(7) -0.0013(6) 0.0009(7) C3 0.0160(8) 0.0149(9) 0.0151(8) -0.0015(7) -0.0014(6) -0.0011(7) C4 0.0197(8) 0.0123(9) 0.0159(8) -0.0023(7) 0.0009(7) -0.0026(7) C5 0.0218(9) 0.0125(9) 0.0182(8) 0.0004(7) -0.0032(7) 0.0044(7) C6 0.0177(8) 0.0195(10) 0.0165(8) -0.0006(7) -0.0046(7) 0.0005(7) O4 0.0282(7) 0.0103(7) 0.0263(7) -0.0008(6) -0.0059(6) -0.0035(6) C11 0.0154(8) 0.0147(9) 0.0182(8) 0.0004(7) -0.0061(7) -0.0004(7) C12 0.0226(9) 0.0157(10) 0.0248(9) -0.0037(8) -0.0054(7) -0.0028(8) C13 0.0226(10) 0.0185(10) 0.0289(10) 0.0021(8) -0.0046(8) -0.0063(8) C14 0.0203(9) 0.0284(12) 0.0199(9) 0.0021(8) -0.0022(7) -0.0036(8) C15 0.0264(10) 0.0293(12) 0.0203(9) -0.0075(8) -0.0023(8) -0.0043(9) C16 0.0226(9) 0.0177(10) 0.0211(9) -0.0023(8) -0.0039(7) -0.0046(8) C7 0.0249(9) 0.0134(9) 0.0266(9) 0.0006(8) -0.0114(8) 0.0004(7) C8 0.0239(9) 0.0192(10) 0.0304(10) -0.0020(8) -0.0114(8) -0.0027(8) _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 1.9210(19) . ? Se1 C11 1.9284(19) . ? C1 C6 1.394(3) . ? C1 C2 1.404(3) . ? C2 C3 1.409(3) . ? C2 C7 1.502(3) . ? C3 C4 1.394(3) . ? C3 C8 1.512(3) . ? C4 O4 1.371(2) . ? C4 C5 1.395(3) . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? O4 H4 0.8400 . ? C11 C16 1.383(3) . ? C11 C12 1.392(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9500 . ? C13 C14 1.384(3) . ? C13 H13 0.9500 . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C15 C16 1.395(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? 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 C11 101.51(8) . . ? C6 C1 C2 121.00(17) . . ? C6 C1 Se1 116.12(14) . . ? C2 C1 Se1 122.76(14) . . ? C1 C2 C3 118.55(17) . . ? C1 C2 C7 122.03(17) . . ? C3 C2 C7 119.42(17) . . ? C4 C3 C2 119.42(17) . . ? C4 C3 C8 119.98(17) . . ? C2 C3 C8 120.60(17) . . ? O4 C4 C3 117.18(17) . . ? O4 C4 C5 121.48(18) . . ? C3 C4 C5 121.34(18) . . ? C6 C5 C4 119.40(18) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C1 120.27(17) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? C4 O4 H4 109.5 . . ? C16 C11 C12 120.50(18) . . ? C16 C11 Se1 123.00(15) . . ? C12 C11 Se1 116.48(15) . . ? C13 C12 C11 119.6(2) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C14 C13 C12 120.4(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 119.59(19) . . ? C13 C14 H14 120.2 . . ? C15 C14 H14 120.2 . . ? C14 C15 C16 120.6(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.29(19) . . ? C11 C16 H16 120.4 . . ? C15 C16 H16 120.4 . . ? C2 C7 H71 109.5 . . ? C2 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? C2 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? C3 C8 H81 109.5 . . ? C3 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C3 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.85 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.264 _refine_diff_density_min -1.127 _refine_diff_density_rms 0.082 #===END data_3 _database_code_CSD 197544 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4,6-bis(phenylseleno)benzene-1,3-diol ; _chemical_name_common 3 _chemical_formula_moiety 'C18 H14 O2 Se2' _chemical_formula_sum 'C18 H14 O2 Se2' _chemical_formula_weight 420.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 15.0339(15) _cell_length_b 5.6420(7) _cell_length_c 18.9279(13) _cell_angle_alpha 90.00 _cell_angle_beta 101.673(7) _cell_angle_gamma 90.00 _cell_volume 1572.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 39.38 _cell_measurement_theta_max 42.48 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 5.911 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.066 _exptl_absorpt_correction_T_max 0.245 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 28 _diffrn_reflns_number 6277 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 74.91 _reflns_number_total 3226 _reflns_number_gt 3203 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing, 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0338P)^2^+2.6447P] 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 SHELXL _refine_ls_extinction_coef 0.00456(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3226 _refine_ls_number_parameters 202 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0302 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0838 _refine_ls_wR_factor_gt 0.0837 _refine_ls_goodness_of_fit_ref 1.224 _refine_ls_restrained_S_all 1.224 _refine_ls_shift/su_max 0.002 _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 0.632094(18) 1.16785(5) 0.593932(14) 0.01987(12) Uani 1 1 d . . . Se2 Se 0.391435(19) 0.37536(5) 0.576191(15) 0.02223(12) Uani 1 1 d . . . C1 C 0.58645(17) 0.9037(5) 0.63848(13) 0.0190(5) Uani 1 1 d . . . C2 C 0.61944(18) 0.8542(6) 0.71185(15) 0.0237(6) Uani 1 1 d . . . C3 C 0.58300(19) 0.6691(6) 0.74507(15) 0.0260(6) Uani 1 1 d . . . H3 H 0.6047 0.6376 0.7949 0.031 Uiso 1 1 calc R . . C4 C 0.51459(18) 0.5303(6) 0.70509(15) 0.0249(6) Uani 1 1 d . . . C5 C 0.47954(17) 0.5803(5) 0.63224(14) 0.0199(5) Uani 1 1 d . . . C6 C 0.51602(16) 0.7679(5) 0.59972(14) 0.0190(5) Uani 1 1 d . . . H6 H 0.4925 0.8036 0.5504 0.023 Uiso 1 1 calc R . . C11 C 0.74639(17) 1.0453(5) 0.57976(13) 0.0175(5) Uani 1 1 d . . . C21 C 0.28634(17) 0.4454(5) 0.61613(14) 0.0191(5) Uani 1 1 d . . . O2 O 0.68820(14) 0.9786(4) 0.75269(10) 0.0314(5) Uani 1 1 d . . . H2 H 0.6970 1.1036 0.7310 0.047 Uiso 1 1 calc R . . O4 O 0.48368(16) 0.3448(4) 0.73919(12) 0.0350(5) Uani 1 1 d . . . H4 H 0.4443 0.2702 0.7097 0.052 Uiso 1 1 calc R . . C12 C 0.78141(18) 0.8269(5) 0.60450(14) 0.0193(5) Uani 1 1 d . . . H12 H 0.7457 0.7192 0.6256 0.023 Uiso 1 1 calc R . . C13 C 0.86931(18) 0.7657(5) 0.59826(15) 0.0223(5) Uani 1 1 d . . . H13 H 0.8938 0.6169 0.6159 0.027 Uiso 1 1 calc R . . C14 C 0.92128(18) 0.9203(6) 0.56644(16) 0.0257(6) Uani 1 1 d . . . H14 H 0.9813 0.8780 0.5626 0.031 Uiso 1 1 calc R . . C15 C 0.8852(2) 1.1368(5) 0.54019(16) 0.0260(6) Uani 1 1 d . . . H15 H 0.9204 1.2417 0.5177 0.031 Uiso 1 1 calc R . . C16 C 0.79785(19) 1.2014(5) 0.54656(14) 0.0219(5) Uani 1 1 d . . . H16 H 0.7733 1.3498 0.5286 0.026 Uiso 1 1 calc R . . C22 C 0.21593(19) 0.2810(6) 0.60185(16) 0.0273(6) Uani 1 1 d . . . H22 H 0.2219 0.1416 0.5750 0.033 Uiso 1 1 calc R . . C23 C 0.1368(2) 0.3227(6) 0.62713(19) 0.0348(7) Uani 1 1 d . . . H23 H 0.0883 0.2118 0.6173 0.042 Uiso 1 1 calc R . . C24 C 0.1282(2) 0.5248(6) 0.66662(17) 0.0311(7) Uani 1 1 d . . . H24 H 0.0740 0.5519 0.6839 0.037 Uiso 1 1 calc R . . C25 C 0.1980(2) 0.6866(6) 0.68089(17) 0.0290(6) Uani 1 1 d . . . H25 H 0.1918 0.8249 0.7081 0.035 Uiso 1 1 calc R . . C26 C 0.2779(2) 0.6485(5) 0.65558(16) 0.0245(6) Uani 1 1 d . . . H26 H 0.3260 0.7606 0.6653 0.029 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 0.01343(17) 0.02399(18) 0.02179(17) 0.00163(10) 0.00262(11) 0.00229(10) Se2 0.01710(18) 0.02549(18) 0.02554(18) -0.00417(11) 0.00771(12) 0.00042(11) C1 0.0119(12) 0.0292(14) 0.0162(11) 0.0022(10) 0.0035(9) 0.0031(10) C2 0.0121(12) 0.0407(17) 0.0179(12) -0.0010(11) 0.0021(10) 0.0018(11) C3 0.0168(13) 0.0442(18) 0.0167(12) 0.0062(11) 0.0024(10) 0.0045(12) C4 0.0177(13) 0.0346(16) 0.0240(13) 0.0078(12) 0.0080(10) 0.0041(11) C5 0.0121(11) 0.0281(14) 0.0198(12) 0.0008(10) 0.0038(9) 0.0031(10) C6 0.0123(12) 0.0290(14) 0.0156(11) 0.0008(10) 0.0023(9) 0.0039(10) C11 0.0165(12) 0.0204(12) 0.0150(11) -0.0040(9) 0.0023(9) -0.0024(10) C21 0.0160(12) 0.0217(13) 0.0193(11) 0.0009(10) 0.0032(9) 0.0021(10) O2 0.0234(10) 0.0502(14) 0.0181(9) 0.0012(9) -0.0019(8) -0.0091(10) O4 0.0297(12) 0.0459(14) 0.0283(11) 0.0151(10) 0.0037(9) -0.0066(10) C12 0.0153(12) 0.0212(13) 0.0210(12) -0.0013(10) 0.0028(10) -0.0029(10) C13 0.0175(13) 0.0222(13) 0.0261(13) -0.0063(11) 0.0017(10) 0.0010(10) C14 0.0149(13) 0.0327(15) 0.0310(14) -0.0123(12) 0.0081(11) -0.0035(11) C15 0.0246(15) 0.0279(15) 0.0281(14) -0.0062(11) 0.0116(11) -0.0083(11) C16 0.0233(14) 0.0226(13) 0.0205(12) -0.0013(10) 0.0062(10) -0.0027(11) C22 0.0198(14) 0.0304(15) 0.0321(15) -0.0097(12) 0.0064(11) -0.0037(12) C23 0.0191(15) 0.0410(18) 0.0442(18) -0.0140(15) 0.0062(13) -0.0092(13) C24 0.0166(13) 0.0434(18) 0.0340(15) -0.0062(14) 0.0069(11) 0.0045(13) C25 0.0276(16) 0.0271(15) 0.0336(15) -0.0091(12) 0.0093(12) 0.0031(12) C26 0.0196(14) 0.0242(14) 0.0306(14) -0.0050(11) 0.0074(11) -0.0002(10) _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 1.907(3) . ? Se1 C11 1.921(3) . ? Se2 C5 1.910(3) . ? Se2 C21 1.925(3) . ? C1 C6 1.390(4) . ? C1 C2 1.405(4) . ? C2 O2 1.355(3) . ? C2 C3 1.387(4) . ? C3 C4 1.389(4) . ? C3 H3 0.9500 . ? C4 O4 1.360(4) . ? C4 C5 1.402(4) . ? C5 C6 1.391(4) . ? C6 H6 0.9500 . ? C11 C12 1.384(4) . ? C11 C16 1.402(4) . ? C21 C26 1.387(4) . ? C21 C22 1.392(4) . ? O2 H2 0.8400 . ? O4 H4 0.8400 . ? C12 C13 1.394(4) . ? C12 H12 0.9500 . ? C13 C14 1.387(4) . ? C13 H13 0.9500 . ? C14 C15 1.387(4) . ? C14 H14 0.9500 . ? C15 C16 1.392(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C22 C23 1.389(4) . ? C22 H22 0.9500 . ? C23 C24 1.384(5) . ? C23 H23 0.9500 . ? C24 C25 1.376(5) . ? C24 H24 0.9500 . ? C25 C26 1.397(5) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C11 101.10(11) . . ? C5 Se2 C21 100.93(11) . . ? C6 C1 C2 119.4(3) . . ? C6 C1 Se1 120.08(19) . . ? C2 C1 Se1 120.4(2) . . ? O2 C2 C3 117.2(2) . . ? O2 C2 C1 122.5(3) . . ? C3 C2 C1 120.3(3) . . ? C2 C3 C4 119.6(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? O4 C4 C3 117.5(2) . . ? O4 C4 C5 121.7(3) . . ? C3 C4 C5 120.8(3) . . ? C6 C5 C4 119.0(3) . . ? C6 C5 Se2 120.39(19) . . ? C4 C5 Se2 120.3(2) . . ? C1 C6 C5 120.8(2) . . ? C1 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C12 C11 C16 120.3(2) . . ? C12 C11 Se1 124.3(2) . . ? C16 C11 Se1 115.3(2) . . ? C26 C21 C22 120.4(3) . . ? C26 C21 Se2 123.5(2) . . ? C22 C21 Se2 116.0(2) . . ? C2 O2 H2 109.5 . . ? C4 O4 H4 109.5 . . ? C11 C12 C13 119.6(3) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.5(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 119.7(3) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 119.4(3) . . ? C15 C16 H16 120.3 . . ? C11 C16 H16 120.3 . . ? C23 C22 C21 119.4(3) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C22 120.4(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 120.1(3) . . ? C25 C24 H24 120.0 . . ? C23 C24 H24 120.0 . . ? C24 C25 C26 120.4(3) . . ? C24 C25 H25 119.8 . . ? C26 C25 H25 119.8 . . ? C21 C26 C25 119.3(3) . . ? C21 C26 H26 120.3 . . ? C25 C26 H26 120.3 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.91 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.431 _refine_diff_density_min -1.408 _refine_diff_density_rms 0.141 #===END data_4 _database_code_CSD 197545 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,2-diethoxy-4,5-bis(phenylseleno)benzene ; _chemical_name_common 4 _chemical_formula_moiety 'C22 H22 O2 Se2' _chemical_formula_sum 'C22 H22 O2 Se2' _chemical_formula_weight 476.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5958(17) _cell_length_b 11.370(3) _cell_length_c 12.388(3) _cell_angle_alpha 116.25(2) _cell_angle_beta 100.280(17) _cell_angle_gamma 104.48(2) _cell_volume 991.4(5) _cell_formula_units_Z 2 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 39.27 _cell_measurement_theta_max 41.50 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 4.761 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.046 _exptl_absorpt_correction_T_max 0.177 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 4.6 _diffrn_reflns_number 6745 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 74.91 _reflns_number_total 3936 _reflns_number_gt 3868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0256P)^2^+2.6667P] 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 3936 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0867 _refine_ls_wR_factor_gt 0.0863 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.001 _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 0.28117(4) 0.04554(3) 0.37247(3) 0.02053(10) Uani 1 1 d . . . Se2 Se 0.57254(4) 0.08358(4) 0.21713(3) 0.02390(10) Uani 1 1 d . . . C1 C 0.5205(4) 0.1570(3) 0.4614(3) 0.0190(6) Uani 1 1 d . . . C2 C 0.6364(4) 0.1751(3) 0.3998(3) 0.0201(6) Uani 1 1 d . . . C3 C 0.8090(4) 0.2590(3) 0.4717(3) 0.0200(6) Uani 1 1 d . . . H3 H 0.8871 0.2763 0.4300 0.024 Uiso 1 1 calc R . . C4 C 0.8663(4) 0.3167(3) 0.6024(3) 0.0178(5) Uani 1 1 d . . . C5 C 0.7494(4) 0.2932(3) 0.6645(3) 0.0167(5) Uani 1 1 d . . . C6 C 0.5776(4) 0.2178(3) 0.5936(3) 0.0188(6) Uani 1 1 d . . . H6 H 0.4976 0.2075 0.6358 0.023 Uiso 1 1 calc R . . C11 C 0.2203(3) 0.1610(3) 0.3107(3) 0.0167(5) Uani 1 1 d . . . C21 C 0.6685(4) -0.0596(3) 0.1868(3) 0.0201(6) Uani 1 1 d . . . O4 O 1.0307(3) 0.3981(2) 0.68057(19) 0.0203(4) Uani 1 1 d . . . O5 O 0.8169(2) 0.3484(2) 0.79215(19) 0.0195(4) Uani 1 1 d . . . C7 C 1.1541(4) 0.4243(4) 0.6205(3) 0.0270(7) Uani 1 1 d . . . H71 H 1.1214 0.4706 0.5736 0.032 Uiso 1 1 calc R . . H72 H 1.1603 0.3343 0.5595 0.032 Uiso 1 1 calc R . . C8 C 1.3232(4) 0.5192(4) 0.7249(3) 0.0357(8) Uani 1 1 d . . . H81 H 1.3531 0.4729 0.7716 0.043 Uiso 1 1 calc R . . H82 H 1.3160 0.6085 0.7837 0.043 Uiso 1 1 calc R . . H83 H 1.4109 0.5379 0.6875 0.043 Uiso 1 1 calc R . . C9 C 0.7061(4) 0.3070(3) 0.8545(3) 0.0206(6) Uani 1 1 d . . . H91 H 0.6302 0.2062 0.7985 0.025 Uiso 1 1 calc R . . H92 H 0.6345 0.3646 0.8737 0.025 Uiso 1 1 calc R . . C10 C 0.8174(4) 0.3301(4) 0.9761(3) 0.0259(6) Uani 1 1 d . . . H101 H 0.8905 0.2752 0.9562 0.031 Uiso 1 1 calc R . . H102 H 0.7457 0.2994 1.0192 0.031 Uiso 1 1 calc R . . H103 H 0.8885 0.4307 1.0321 0.031 Uiso 1 1 calc R . . C12 C 0.0769(4) 0.0963(3) 0.2035(3) 0.0219(6) Uani 1 1 d . . . H12 H 0.0191 -0.0034 0.1584 0.026 Uiso 1 1 calc R . . C13 C 0.0177(4) 0.1774(4) 0.1620(3) 0.0273(7) Uani 1 1 d . . . H13 H -0.0816 0.1330 0.0893 0.033 Uiso 1 1 calc R . . C14 C 0.1031(4) 0.3230(3) 0.2264(3) 0.0239(6) Uani 1 1 d . . . H14 H 0.0625 0.3783 0.1980 0.029 Uiso 1 1 calc R . . C15 C 0.2482(4) 0.3869(3) 0.3324(3) 0.0223(6) Uani 1 1 d . . . H15 H 0.3075 0.4863 0.3760 0.027 Uiso 1 1 calc R . . C16 C 0.3074(4) 0.3073(3) 0.3754(3) 0.0197(6) Uani 1 1 d . . . H16 H 0.4066 0.3519 0.4482 0.024 Uiso 1 1 calc R . . C22 C 0.6452(4) -0.1526(3) 0.0598(3) 0.0256(6) Uani 1 1 d . . . H22 H 0.5865 -0.1426 -0.0063 0.031 Uiso 1 1 calc R . . C23 C 0.7087(4) -0.2603(4) 0.0307(3) 0.0326(7) Uani 1 1 d . . . H23 H 0.6933 -0.3239 -0.0556 0.039 Uiso 1 1 calc R . . C24 C 0.7943(4) -0.2750(4) 0.1272(4) 0.0310(7) Uani 1 1 d . . . H24 H 0.8378 -0.3483 0.1071 0.037 Uiso 1 1 calc R . . C25 C 0.8160(4) -0.1826(3) 0.2524(3) 0.0275(7) Uani 1 1 d . . . H25 H 0.8745 -0.1929 0.3185 0.033 Uiso 1 1 calc R . . C26 C 0.7533(4) -0.0750(3) 0.2832(3) 0.0225(6) Uani 1 1 d . . . H26 H 0.7684 -0.0123 0.3697 0.027 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 0.01776(16) 0.01916(16) 0.02565(17) 0.01470(13) 0.00223(12) 0.00569(12) Se2 0.02744(18) 0.03204(18) 0.02148(17) 0.01706(14) 0.00834(13) 0.01858(14) C1 0.0166(13) 0.0194(13) 0.0264(14) 0.0142(12) 0.0071(11) 0.0100(11) C2 0.0236(14) 0.0218(13) 0.0219(14) 0.0140(12) 0.0077(12) 0.0140(12) C3 0.0212(14) 0.0236(14) 0.0274(15) 0.0177(12) 0.0141(12) 0.0139(12) C4 0.0158(13) 0.0174(12) 0.0249(14) 0.0126(11) 0.0081(11) 0.0092(11) C5 0.0182(13) 0.0173(12) 0.0206(13) 0.0121(11) 0.0083(11) 0.0097(11) C6 0.0182(13) 0.0192(13) 0.0259(14) 0.0150(12) 0.0098(12) 0.0094(11) C11 0.0145(12) 0.0203(13) 0.0217(13) 0.0135(11) 0.0086(11) 0.0092(11) C21 0.0178(13) 0.0230(14) 0.0236(14) 0.0136(12) 0.0092(11) 0.0093(11) O4 0.0149(9) 0.0233(10) 0.0249(10) 0.0134(9) 0.0090(8) 0.0068(8) O5 0.0167(9) 0.0228(10) 0.0188(9) 0.0115(8) 0.0071(8) 0.0046(8) C7 0.0235(15) 0.0321(16) 0.0321(16) 0.0191(14) 0.0171(14) 0.0100(13) C8 0.0199(15) 0.0416(19) 0.0367(18) 0.0166(16) 0.0130(14) 0.0017(14) C9 0.0169(13) 0.0262(14) 0.0242(14) 0.0155(12) 0.0108(12) 0.0086(11) C10 0.0211(14) 0.0342(16) 0.0234(15) 0.0167(13) 0.0078(12) 0.0081(13) C12 0.0199(14) 0.0210(14) 0.0238(14) 0.0126(12) 0.0043(12) 0.0061(12) C13 0.0224(15) 0.0316(16) 0.0297(16) 0.0181(14) 0.0038(13) 0.0117(13) C14 0.0238(15) 0.0282(15) 0.0309(16) 0.0204(13) 0.0103(13) 0.0156(13) C15 0.0219(14) 0.0198(13) 0.0308(15) 0.0146(12) 0.0108(12) 0.0119(12) C16 0.0174(13) 0.0194(13) 0.0222(14) 0.0108(12) 0.0048(11) 0.0075(11) C22 0.0201(14) 0.0302(16) 0.0242(15) 0.0129(13) 0.0073(12) 0.0078(12) C23 0.0288(17) 0.0280(16) 0.0329(17) 0.0095(14) 0.0145(14) 0.0072(14) C24 0.0267(16) 0.0261(15) 0.046(2) 0.0178(15) 0.0190(15) 0.0157(13) C25 0.0225(15) 0.0288(16) 0.0385(18) 0.0212(14) 0.0109(14) 0.0123(13) C26 0.0207(14) 0.0243(14) 0.0256(15) 0.0146(12) 0.0083(12) 0.0092(12) _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 C11 1.917(3) . ? Se1 C1 1.924(3) . ? Se2 C2 1.921(3) . ? Se2 C21 1.927(3) . ? C1 C2 1.387(4) . ? C1 C6 1.394(4) . ? C2 C3 1.405(4) . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 O4 1.362(3) . ? C4 C5 1.413(4) . ? C5 O5 1.358(3) . ? C5 C6 1.388(4) . ? C6 H6 0.9500 . ? C11 C12 1.387(4) . ? C11 C16 1.397(4) . ? C21 C26 1.388(4) . ? C21 C22 1.394(4) . ? O4 C7 1.444(3) . ? O5 C9 1.445(3) . ? C7 C8 1.503(5) . ? C7 H71 0.9900 . ? C7 H72 0.9900 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? C9 C10 1.504(4) . ? C9 H91 0.9900 . ? C9 H92 0.9900 . ? C10 H101 0.9800 . ? C10 H102 0.9800 . ? C10 H103 0.9800 . ? C12 C13 1.390(4) . ? C12 H12 0.9500 . ? C13 C14 1.389(5) . ? C13 H13 0.9500 . ? C14 C15 1.388(4) . ? C14 H14 0.9500 . ? C15 C16 1.387(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C22 C23 1.393(5) . ? C22 H22 0.9500 . ? C23 C24 1.386(5) . ? C23 H23 0.9500 . ? C24 C25 1.380(5) . ? C24 H24 0.9500 . ? C25 C26 1.386(4) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? 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 C11 Se1 C1 99.22(12) . . ? C2 Se2 C21 98.95(12) . . ? C2 C1 C6 119.6(3) . . ? C2 C1 Se1 123.1(2) . . ? C6 C1 Se1 117.2(2) . . ? C1 C2 C3 119.7(3) . . ? C1 C2 Se2 122.6(2) . . ? C3 C2 Se2 117.7(2) . . ? C4 C3 C2 120.7(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? O4 C4 C3 125.3(3) . . ? O4 C4 C5 115.1(2) . . ? C3 C4 C5 119.6(3) . . ? O5 C5 C6 124.9(3) . . ? O5 C5 C4 115.9(2) . . ? C6 C5 C4 119.2(3) . . ? C5 C6 C1 121.1(3) . . ? C5 C6 H6 119.5 . . ? C1 C6 H6 119.5 . . ? C12 C11 C16 120.0(3) . . ? C12 C11 Se1 117.7(2) . . ? C16 C11 Se1 122.2(2) . . ? C26 C21 C22 120.1(3) . . ? C26 C21 Se2 123.5(2) . . ? C22 C21 Se2 116.4(2) . . ? C4 O4 C7 116.7(2) . . ? C5 O5 C9 117.1(2) . . ? O4 C7 C8 107.1(3) . . ? O4 C7 H71 110.3 . . ? C8 C7 H71 110.3 . . ? O4 C7 H72 110.3 . . ? C8 C7 H72 110.3 . . ? H71 C7 H72 108.5 . . ? C7 C8 H81 109.5 . . ? C7 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C7 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? O5 C9 C10 107.5(2) . . ? O5 C9 H91 110.2 . . ? C10 C9 H91 110.2 . . ? O5 C9 H92 110.2 . . ? C10 C9 H92 110.2 . . ? H91 C9 H92 108.5 . . ? C9 C10 H101 109.5 . . ? C9 C10 H102 109.5 . . ? H101 C10 H102 109.5 . . ? C9 C10 H103 109.5 . . ? H101 C10 H103 109.5 . . ? H102 C10 H103 109.5 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.5(3) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C16 C15 C14 120.7(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C11 119.5(3) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? C23 C22 C21 119.5(3) . . ? C23 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? C24 C23 C22 120.3(3) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.6(3) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 120.8(3) . . ? C24 C25 H25 119.6 . . ? C26 C25 H25 119.6 . . ? C25 C26 C21 119.6(3) . . ? C25 C26 H26 120.2 . . ? C21 C26 H26 120.2 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 74.91 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.960 _refine_diff_density_min -0.912 _refine_diff_density_rms 0.089 #===END data_5 _database_code_CSD 197546 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,4-dimethoxy-2,5-bis(phenylseleno)benzene ; _chemical_name_common 5 _chemical_formula_moiety 'C20 H18 O2 Se2' _chemical_formula_sum 'C20 H18 O2 Se2' _chemical_formula_weight 448.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 7.1618(10) _cell_length_b 15.1320(19) _cell_length_c 8.2912(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.609(11) _cell_angle_gamma 90.00 _cell_volume 873.31(19) _cell_formula_units_Z 2 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 39.52 _cell_measurement_theta_max 42.38 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.705 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 5.363 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.046 _exptl_absorpt_correction_T_max 0.208 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 4.0 _diffrn_reflns_number 4116 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.85 _diffrn_reflns_theta_max 74.93 _reflns_number_total 1797 _reflns_number_gt 1748 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0603P)^2^+0.7230P] 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 SHELXL _refine_ls_extinction_coef 0.0082(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1797 _refine_ls_number_parameters 111 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0352 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0958 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _refine_ls_shift/su_max 0.001 _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 0.28515(4) 0.431411(16) 0.76467(3) 0.02065(17) Uani 1 1 d . . . C1 C 0.1217(3) 0.47618(15) 0.8991(3) 0.0177(4) Uani 1 1 d . . . C2 C -0.0431(3) 0.58819(17) 1.0169(3) 0.0179(4) Uani 1 1 d . . . C3 C 0.0797(4) 0.56519(14) 0.9163(3) 0.0181(5) Uani 1 1 d . . . H3 H 0.1341 0.6095 0.8601 0.022 Uiso 1 1 calc R . . O2 O -0.0978(3) 0.67351(11) 1.0408(2) 0.0235(4) Uani 1 1 d . . . C4 C 0.0114(4) 0.74346(16) 0.9929(3) 0.0248(5) Uani 1 1 d . . . H41 H -0.0100 0.7445 0.8717 0.030 Uiso 1 1 calc R . . H42 H 0.1482 0.7340 1.0426 0.030 Uiso 1 1 calc R . . H43 H -0.0290 0.8000 1.0314 0.030 Uiso 1 1 calc R . . C11 C 0.3477(3) 0.53719(16) 0.6609(3) 0.0182(4) Uani 1 1 d . . . C12 C 0.4882(3) 0.59491(17) 0.7468(3) 0.0219(5) Uani 1 1 d . . . H12 H 0.5422 0.5866 0.8620 0.026 Uiso 1 1 calc R . . C13 C 0.5485(4) 0.66474(17) 0.6624(3) 0.0260(5) Uani 1 1 d . . . H13 H 0.6434 0.7046 0.7203 0.031 Uiso 1 1 calc R . . C14 C 0.4705(4) 0.67652(17) 0.4936(3) 0.0273(5) Uani 1 1 d . . . H14 H 0.5128 0.7240 0.4363 0.033 Uiso 1 1 calc R . . C15 C 0.3314(4) 0.61895(18) 0.4096(3) 0.0262(5) Uani 1 1 d . . . H15 H 0.2784 0.6270 0.2942 0.031 Uiso 1 1 calc R . . C16 C 0.2684(4) 0.54932(18) 0.4925(3) 0.0218(5) Uani 1 1 d . . . H16 H 0.1718 0.5103 0.4345 0.026 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 0.0241(2) 0.0199(2) 0.0221(2) 0.00046(8) 0.01381(14) 0.00013(8) C1 0.0155(10) 0.0222(11) 0.0167(10) -0.0006(8) 0.0064(8) -0.0005(8) C2 0.0172(10) 0.0191(10) 0.0179(10) 0.0006(9) 0.0052(8) 0.0007(9) C3 0.0178(11) 0.0204(12) 0.0179(12) 0.0026(7) 0.0075(9) -0.0015(7) O2 0.0278(9) 0.0174(8) 0.0297(9) 0.0019(7) 0.0157(7) -0.0002(7) C4 0.0291(12) 0.0188(11) 0.0288(12) 0.0042(9) 0.0115(10) -0.0024(9) C11 0.0177(10) 0.0221(11) 0.0169(10) 0.0007(9) 0.0084(8) 0.0012(9) C12 0.0203(11) 0.0286(12) 0.0179(10) -0.0032(9) 0.0067(9) -0.0014(10) C13 0.0252(11) 0.0252(12) 0.0306(13) -0.0046(10) 0.0130(10) -0.0032(9) C14 0.0341(13) 0.0226(12) 0.0324(13) 0.0064(10) 0.0222(11) 0.0057(10) C15 0.0308(12) 0.0319(13) 0.0184(11) 0.0056(9) 0.0108(9) 0.0118(10) C16 0.0197(11) 0.0289(11) 0.0176(11) -0.0023(10) 0.0061(9) 0.0038(10) _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 C11 1.919(2) . ? Se1 C1 1.920(2) . ? C1 C2 1.391(3) 3_567 ? C1 C3 1.395(3) . ? C2 O2 1.377(3) . ? C2 C1 1.391(3) 3_567 ? C2 C3 1.392(4) . ? C3 H3 0.9500 . ? O2 C4 1.427(3) . ? C4 H41 0.9800 . ? C4 H42 0.9800 . ? C4 H43 0.9800 . ? C11 C16 1.390(3) . ? C11 C12 1.395(3) . ? C12 C13 1.391(4) . ? C12 H12 0.9500 . ? C13 C14 1.390(4) . ? C13 H13 0.9500 . ? C14 C15 1.383(4) . ? C14 H14 0.9500 . ? C15 C16 1.390(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C11 Se1 C1 101.80(10) . . ? C2 C1 C3 120.2(2) 3_567 . ? C2 C1 Se1 114.67(18) 3_567 . ? C3 C1 Se1 125.15(18) . . ? O2 C2 C1 115.0(2) . 3_567 ? O2 C2 C3 124.2(2) . . ? C1 C2 C3 120.8(2) 3_567 . ? C2 C3 C1 119.0(2) . . ? C2 C3 H3 120.5 . . ? C1 C3 H3 120.5 . . ? C2 O2 C4 117.54(19) . . ? O2 C4 H41 109.5 . . ? O2 C4 H42 109.5 . . ? H41 C4 H42 109.5 . . ? O2 C4 H43 109.5 . . ? H41 C4 H43 109.5 . . ? H42 C4 H43 109.5 . . ? C16 C11 C12 120.4(2) . . ? C16 C11 Se1 118.51(18) . . ? C12 C11 Se1 120.62(17) . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.9(2) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 119.6(2) . . ? C11 C16 H16 120.2 . . ? C15 C16 H16 120.2 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 74.93 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.713 _refine_diff_density_min -1.179 _refine_diff_density_rms 0.125 #===END data_6 _database_code_CSD 197547 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-methoxy-3,5-dimethyl-4-(phenylseleno)benzene ; _chemical_name_common 6 _chemical_formula_moiety 'C15 H16 O Se' _chemical_formula_sum 'C15 H16 O Se' _chemical_formula_weight 291.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.2789(7) _cell_length_b 9.4958(8) _cell_length_c 19.043(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.047(11) _cell_angle_gamma 90.00 _cell_volume 1306.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 39.36 _cell_measurement_theta_max 42.55 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 3.724 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.066 _exptl_absorpt_correction_T_max 0.223 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 6618 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.68 _diffrn_reflns_theta_max 74.91 _reflns_number_total 2676 _reflns_number_gt 2608 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0412P)^2^+0.8552P] 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 SHELXL _refine_ls_extinction_coef 0.0046(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2676 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0262 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0697 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 0.06281(3) 0.819660(19) 0.965997(9) 0.02797(10) Uani 1 1 d . . . C1 C -0.0276(2) 0.65218(18) 0.91605(9) 0.0218(3) Uani 1 1 d . . . C2 C -0.2100(2) 0.64991(18) 0.88111(9) 0.0233(3) Uani 1 1 d . . . C3 C -0.2765(2) 0.52540(18) 0.84940(9) 0.0225(3) Uani 1 1 d . . . H3 H -0.3993 0.5222 0.8258 0.027 Uiso 1 1 calc R . . C4 C -0.1667(2) 0.40501(17) 0.85150(8) 0.0197(3) Uani 1 1 d . . . C5 C 0.0137(2) 0.40870(17) 0.88568(8) 0.0202(3) Uani 1 1 d . . . H5 H 0.0887 0.3266 0.8870 0.024 Uiso 1 1 calc R . . C6 C 0.0847(2) 0.53244(18) 0.91793(8) 0.0207(3) Uani 1 1 d . . . O4 O -0.24821(16) 0.28912(13) 0.81872(7) 0.0251(3) Uani 1 1 d . . . C7 C -0.3338(3) 0.7772(2) 0.87628(12) 0.0363(4) Uani 1 1 d . . . H71 H -0.4450 0.7583 0.8432 0.044 Uiso 1 1 calc R . . H72 H -0.2676 0.8579 0.8594 0.044 Uiso 1 1 calc R . . H73 H -0.3694 0.7985 0.9231 0.044 Uiso 1 1 calc R . . C8 C -0.1405(3) 0.16264(18) 0.82211(10) 0.0281(4) Uani 1 1 d . . . H81 H -0.2126 0.0872 0.7967 0.034 Uiso 1 1 calc R . . H82 H -0.1078 0.1352 0.8717 0.034 Uiso 1 1 calc R . . H83 H -0.0272 0.1789 0.8003 0.034 Uiso 1 1 calc R . . C9 C 0.2812(2) 0.5317(2) 0.95354(10) 0.0283(4) Uani 1 1 d . . . H91 H 0.2823 0.5526 1.0040 0.034 Uiso 1 1 calc R . . H92 H 0.3531 0.6033 0.9318 0.034 Uiso 1 1 calc R . . H93 H 0.3361 0.4387 0.9480 0.034 Uiso 1 1 calc R . . C11 C 0.1817(2) 0.91201(18) 0.89421(9) 0.0229(3) Uani 1 1 d . . . C12 C 0.3038(2) 1.02163(19) 0.91539(10) 0.0284(4) Uani 1 1 d . . . H12 H 0.3248 1.0484 0.9638 0.034 Uiso 1 1 calc R . . C13 C 0.3942(3) 1.0914(2) 0.86564(13) 0.0365(4) Uani 1 1 d . . . H13 H 0.4763 1.1666 0.8800 0.044 Uiso 1 1 calc R . . C14 C 0.3654(3) 1.0517(2) 0.79489(12) 0.0372(5) Uani 1 1 d . . . H14 H 0.4292 1.0986 0.7611 0.045 Uiso 1 1 calc R . . C15 C 0.2432(3) 0.9436(2) 0.77391(10) 0.0323(4) Uani 1 1 d . . . H15 H 0.2232 0.9165 0.7256 0.039 Uiso 1 1 calc R . . C16 C 0.1497(2) 0.87442(19) 0.82317(9) 0.0259(3) Uani 1 1 d . . . H16 H 0.0640 0.8016 0.8084 0.031 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 0.03985(15) 0.02309(14) 0.02289(13) -0.00467(6) 0.01151(8) -0.01026(7) C1 0.0259(8) 0.0198(7) 0.0203(7) 0.0004(6) 0.0057(6) -0.0047(6) C2 0.0245(8) 0.0212(8) 0.0251(8) 0.0046(6) 0.0064(6) 0.0010(6) C3 0.0196(7) 0.0241(8) 0.0236(8) 0.0042(6) 0.0015(6) 0.0006(6) C4 0.0219(7) 0.0197(8) 0.0178(7) 0.0011(6) 0.0034(6) -0.0033(6) C5 0.0209(7) 0.0199(8) 0.0202(7) 0.0022(6) 0.0045(6) 0.0013(6) C6 0.0202(7) 0.0239(8) 0.0181(7) 0.0031(6) 0.0037(5) -0.0025(6) O4 0.0242(6) 0.0206(6) 0.0293(6) -0.0035(5) -0.0009(5) -0.0018(5) C7 0.0329(9) 0.0237(9) 0.0522(12) 0.0018(9) 0.0055(8) 0.0055(8) C8 0.0322(9) 0.0213(8) 0.0306(9) -0.0057(7) 0.0037(7) -0.0001(7) C9 0.0219(8) 0.0326(10) 0.0292(9) 0.0008(7) -0.0018(6) -0.0042(7) C11 0.0228(7) 0.0184(8) 0.0283(8) 0.0015(6) 0.0064(6) 0.0021(6) C12 0.0255(8) 0.0205(8) 0.0401(10) -0.0022(7) 0.0071(7) 0.0000(7) C13 0.0272(9) 0.0217(9) 0.0626(13) 0.0051(9) 0.0143(8) -0.0009(7) C14 0.0305(9) 0.0326(10) 0.0519(12) 0.0199(9) 0.0189(8) 0.0073(8) C15 0.0306(9) 0.0370(10) 0.0309(9) 0.0109(8) 0.0102(7) 0.0104(8) C16 0.0274(8) 0.0245(9) 0.0269(8) 0.0021(7) 0.0073(6) 0.0016(7) _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 C11 1.9177(17) . ? Se1 C1 1.9270(17) . ? C1 C6 1.398(2) . ? C1 C2 1.410(2) . ? C2 C3 1.388(2) . ? C2 C7 1.504(2) . ? C3 C4 1.393(2) . ? C3 H3 0.9500 . ? C4 O4 1.365(2) . ? C4 C5 1.392(2) . ? C5 C6 1.395(2) . ? C5 H5 0.9500 . ? C6 C9 1.506(2) . ? O4 C8 1.432(2) . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? C9 H91 0.9800 . ? C9 H92 0.9800 . ? C9 H93 0.9800 . ? C11 C16 1.391(2) . ? C11 C12 1.396(2) . ? C12 C13 1.387(3) . ? C12 H12 0.9500 . ? C13 C14 1.390(3) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C11 Se1 C1 100.49(7) . . ? C6 C1 C2 120.87(15) . . ? C6 C1 Se1 119.70(12) . . ? C2 C1 Se1 119.35(13) . . ? C3 C2 C1 118.45(16) . . ? C3 C2 C7 118.94(16) . . ? C1 C2 C7 122.61(17) . . ? C2 C3 C4 121.23(15) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? O4 C4 C5 124.49(15) . . ? O4 C4 C3 115.66(14) . . ? C5 C4 C3 119.85(15) . . ? C4 C5 C6 120.27(15) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.33(14) . . ? C5 C6 C9 118.31(15) . . ? C1 C6 C9 122.36(15) . . ? C4 O4 C8 116.80(13) . . ? C2 C7 H71 109.5 . . ? C2 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? C2 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? O4 C8 H81 109.5 . . ? O4 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? O4 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? C6 C9 H91 109.5 . . ? C6 C9 H92 109.5 . . ? H91 C9 H92 109.5 . . ? C6 C9 H93 109.5 . . ? H91 C9 H93 109.5 . . ? H92 C9 H93 109.5 . . ? C16 C11 C12 119.84(16) . . ? C16 C11 Se1 122.65(13) . . ? C12 C11 Se1 117.51(13) . . ? C13 C12 C11 119.82(18) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.34(19) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C15 C14 C13 119.73(17) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.41(19) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C11 119.83(18) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.91 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.490 _refine_diff_density_min -0.792 _refine_diff_density_rms 0.062 #===END data_7 _database_code_CSD 197548 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-(phenylseleno)benzene-1,3-diol ; _chemical_name_common 7 _chemical_formula_moiety 'C12 H10 O2 Se' _chemical_formula_sum 'C12 H10 O2 Se' _chemical_formula_weight 265.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7061(11) _cell_length_b 10.3054(8) _cell_length_c 11.8008(13) _cell_angle_alpha 92.369(8) _cell_angle_beta 90.070(10) _cell_angle_gamma 94.027(9) _cell_volume 1055.24(19) _cell_formula_units_Z 4 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 37.65 _cell_measurement_theta_max 42.48 _exptl_crystal_description 'thin plate' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.669 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 4.622 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.071 _exptl_absorpt_correction_T_max 0.225 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 11170 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0097 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.75 _diffrn_reflns_theta_max 74.87 _reflns_number_total 4334 _reflns_number_gt 4320 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0412P)^2^+1.4749P] 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 SHELXL _refine_ls_extinction_coef 0.0092(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4334 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0292 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0783 _refine_ls_wR_factor_gt 0.0782 _refine_ls_goodness_of_fit_ref 1.115 _refine_ls_restrained_S_all 1.115 _refine_ls_shift/su_max 0.002 _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 Se1A Se 0.26728(3) 0.89611(2) 1.108819(18) 0.01808(10) Uani 1 1 d . . . C1A C 0.1735(2) 0.9193(2) 0.96564(18) 0.0163(4) Uani 1 1 d . . . C2A C 0.0670(3) 0.8249(2) 0.91840(18) 0.0163(4) Uani 1 1 d . . . O2A O 0.0311(2) 0.70824(15) 0.96704(13) 0.0214(3) Uani 1 1 d . . . H2A H 0.0756 0.7076 1.0302 0.032 Uiso 1 1 calc R . . C3A C -0.0065(3) 0.8440(2) 0.81666(19) 0.0176(4) Uani 1 1 d . . . H3A H -0.0800 0.7796 0.7857 0.021 Uiso 1 1 calc R . . C4A C 0.0281(2) 0.9580(2) 0.76034(18) 0.0162(4) Uani 1 1 d . . . O4A O -0.04664(19) 0.96929(15) 0.65941(13) 0.0196(3) Uani 1 1 d . . . H4A H -0.0127 1.0377 0.6290 0.029 Uiso 1 1 calc R . . C5A C 0.1326(3) 1.0546(2) 0.80668(19) 0.0189(4) Uani 1 1 d . . . H5A H 0.1549 1.1331 0.7686 0.023 Uiso 1 1 calc R . . C6A C 0.2033(2) 1.0345(2) 0.90913(19) 0.0181(4) Uani 1 1 d . . . H6A H 0.2736 1.1005 0.9415 0.022 Uiso 1 1 calc R . . C11A C 0.4213(2) 0.7778(2) 1.0666(2) 0.0186(4) Uani 1 1 d . . . C12A C 0.4649(3) 0.7503(2) 0.9558(2) 0.0221(5) Uani 1 1 d . . . H12A H 0.4162 0.7882 0.8944 0.027 Uiso 1 1 calc R . . C13A C 0.5816(3) 0.6662(2) 0.9358(2) 0.0293(5) Uani 1 1 d . . . H13A H 0.6116 0.6457 0.8602 0.035 Uiso 1 1 calc R . . C14A C 0.6541(3) 0.6120(2) 1.0254(3) 0.0314(6) Uani 1 1 d . . . H14A H 0.7343 0.5556 1.0112 0.038 Uiso 1 1 calc R . . C15A C 0.6095(3) 0.6403(3) 1.1350(3) 0.0334(6) Uani 1 1 d . . . H15A H 0.6589 0.6032 1.1965 0.040 Uiso 1 1 calc R . . C16A C 0.4927(3) 0.7228(3) 1.1560(2) 0.0280(5) Uani 1 1 d . . . H16A H 0.4616 0.7416 1.2317 0.034 Uiso 1 1 calc R . . Se1B Se 0.25156(3) 0.37806(2) 0.397240(19) 0.01905(10) Uani 1 1 d . . . C1B C 0.1674(2) 0.4051(2) 0.54499(18) 0.0167(4) Uani 1 1 d . . . C2B C 0.0631(3) 0.3120(2) 0.59121(19) 0.0175(4) Uani 1 1 d . . . O2B O 0.0277(2) 0.19246(15) 0.54009(14) 0.0225(3) Uani 1 1 d . . . H2B H 0.0665 0.1898 0.4750 0.034 Uiso 1 1 calc R . . C3B C -0.0082(3) 0.3378(2) 0.69369(19) 0.0181(4) Uani 1 1 d . . . H3B H -0.0798 0.2745 0.7238 0.022 Uiso 1 1 calc R . . C4B C 0.0247(3) 0.4560(2) 0.75258(18) 0.0174(4) Uani 1 1 d . . . O4B O -0.0493(2) 0.47330(16) 0.85336(14) 0.0221(3) Uani 1 1 d . . . H4B H -0.0177 0.5450 0.8845 0.033 Uiso 1 1 calc R . . C5B C 0.1289(3) 0.5499(2) 0.7085(2) 0.0195(4) Uani 1 1 d . . . H5B H 0.1520 0.6308 0.7487 0.023 Uiso 1 1 calc R . . C6B C 0.1981(3) 0.5233(2) 0.6052(2) 0.0197(4) Uani 1 1 d . . . H6B H 0.2683 0.5873 0.5746 0.024 Uiso 1 1 calc R . . C11B C 0.4083(3) 0.2604(2) 0.42557(19) 0.0188(4) Uani 1 1 d . . . C12B C 0.4973(3) 0.2692(2) 0.5236(2) 0.0235(5) Uani 1 1 d . . . H12B H 0.4765 0.3298 0.5834 0.028 Uiso 1 1 calc R . . C13B C 0.6178(3) 0.1877(3) 0.5331(2) 0.0287(5) Uani 1 1 d . . . H13B H 0.6781 0.1923 0.6005 0.034 Uiso 1 1 calc R . . C14B C 0.6503(3) 0.1006(3) 0.4458(2) 0.0302(6) Uani 1 1 d . . . H14B H 0.7342 0.0473 0.4523 0.036 Uiso 1 1 calc R . . C15B C 0.5599(3) 0.0914(3) 0.3486(2) 0.0299(5) Uani 1 1 d . . . H15B H 0.5815 0.0311 0.2887 0.036 Uiso 1 1 calc R . . C16B C 0.4376(3) 0.1702(2) 0.3387(2) 0.0248(5) Uani 1 1 d . . . H16B H 0.3743 0.1625 0.2728 0.030 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 Se1A 0.01943(14) 0.02122(14) 0.01375(14) -0.00025(9) -0.00085(9) 0.00316(9) C1A 0.0161(10) 0.0178(10) 0.0155(10) 0.0007(8) 0.0000(8) 0.0030(8) C2A 0.0191(10) 0.0140(10) 0.0161(10) 0.0016(8) 0.0021(8) 0.0020(8) O2A 0.0301(9) 0.0166(7) 0.0171(8) 0.0049(6) -0.0034(6) -0.0032(6) C3A 0.0197(10) 0.0155(10) 0.0175(10) -0.0011(8) -0.0011(8) 0.0004(8) C4A 0.0172(10) 0.0185(10) 0.0134(10) 0.0002(8) 0.0007(8) 0.0053(8) O4A 0.0259(8) 0.0172(7) 0.0156(7) 0.0023(6) -0.0042(6) 0.0004(6) C5A 0.0202(10) 0.0166(10) 0.0202(11) 0.0025(8) 0.0014(8) 0.0019(8) C6A 0.0166(10) 0.0173(10) 0.0201(11) -0.0002(8) -0.0001(8) 0.0002(8) C11A 0.0159(10) 0.0176(10) 0.0222(11) 0.0035(8) 0.0007(8) 0.0002(8) C12A 0.0226(11) 0.0221(11) 0.0220(11) 0.0028(9) 0.0031(9) 0.0020(9) C13A 0.0288(13) 0.0248(12) 0.0344(14) 0.0006(10) 0.0106(11) 0.0021(10) C14A 0.0203(11) 0.0203(12) 0.0548(17) 0.0077(11) 0.0065(11) 0.0053(9) C15A 0.0263(13) 0.0332(14) 0.0425(16) 0.0142(12) -0.0041(11) 0.0063(11) C16A 0.0274(13) 0.0337(13) 0.0240(12) 0.0075(10) -0.0013(10) 0.0060(10) Se1B 0.02297(15) 0.02022(14) 0.01453(14) 0.00369(9) 0.00167(9) 0.00377(9) C1B 0.0191(10) 0.0164(10) 0.0149(10) 0.0042(8) 0.0023(8) 0.0015(8) C2B 0.0201(10) 0.0149(10) 0.0176(10) 0.0026(8) -0.0019(8) 0.0014(8) O2B 0.0329(9) 0.0172(8) 0.0168(8) -0.0002(6) 0.0049(7) -0.0029(6) C3B 0.0202(10) 0.0154(10) 0.0188(10) 0.0039(8) -0.0009(8) -0.0003(8) C4B 0.0193(10) 0.0175(10) 0.0162(10) 0.0031(8) 0.0016(8) 0.0043(8) O4B 0.0293(9) 0.0185(8) 0.0181(8) 0.0000(6) 0.0058(6) 0.0003(6) C5B 0.0224(11) 0.0144(10) 0.0218(11) 0.0016(8) 0.0005(9) 0.0022(8) C6B 0.0203(10) 0.0158(10) 0.0233(11) 0.0036(8) 0.0019(8) 0.0011(8) C11B 0.0171(10) 0.0200(10) 0.0193(10) 0.0049(8) 0.0040(8) -0.0007(8) C12B 0.0234(11) 0.0271(12) 0.0201(11) 0.0025(9) 0.0016(9) 0.0016(9) C13B 0.0228(12) 0.0365(14) 0.0275(13) 0.0073(11) -0.0024(10) 0.0033(10) C14B 0.0223(12) 0.0343(14) 0.0354(14) 0.0094(11) 0.0060(10) 0.0086(10) C15B 0.0306(13) 0.0307(13) 0.0294(13) -0.0004(10) 0.0085(10) 0.0091(10) C16B 0.0266(12) 0.0279(12) 0.0203(11) -0.0001(9) 0.0022(9) 0.0048(10) _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 Se1A C1A 1.907(2) . ? Se1A C11A 1.928(2) . ? C1A C6A 1.394(3) . ? C1A C2A 1.394(3) . ? C2A O2A 1.370(3) . ? C2A C3A 1.387(3) . ? O2A H2A 0.8400 . ? C3A C4A 1.389(3) . ? C3A H3A 0.9500 . ? C4A O4A 1.370(3) . ? C4A C5A 1.394(3) . ? O4A H4A 0.8400 . ? C5A C6A 1.386(3) . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C11A C16A 1.385(3) . ? C11A C12A 1.385(3) . ? C12A C13A 1.395(3) . ? C12A H12A 0.9500 . ? C13A C14A 1.387(4) . ? C13A H13A 0.9500 . ? C14A C15A 1.377(4) . ? C14A H14A 0.9500 . ? C15A C16A 1.387(4) . ? C15A H15A 0.9500 . ? C16A H16A 0.9500 . ? Se1B C1B 1.910(2) . ? Se1B C11B 1.926(2) . ? C1B C6B 1.394(3) . ? C1B C2B 1.401(3) . ? C2B O2B 1.365(3) . ? C2B C3B 1.384(3) . ? O2B H2B 0.8400 . ? C3B C4B 1.390(3) . ? C3B H3B 0.9500 . ? C4B O4B 1.364(3) . ? C4B C5B 1.396(3) . ? O4B H4B 0.8400 . ? C5B C6B 1.387(3) . ? C5B H5B 0.9500 . ? C6B H6B 0.9500 . ? C11B C12B 1.388(3) . ? C11B C16B 1.391(3) . ? C12B C13B 1.395(4) . ? C12B H12B 0.9500 . ? C13B C14B 1.382(4) . ? C13B H13B 0.9500 . ? C14B C15B 1.385(4) . ? C14B H14B 0.9500 . ? C15B C16B 1.392(4) . ? C15B H15B 0.9500 . ? C16B H16B 0.9500 . ? 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 C1A Se1A C11A 101.21(9) . . ? C6A C1A C2A 118.5(2) . . ? C6A C1A Se1A 120.54(16) . . ? C2A C1A Se1A 120.81(16) . . ? O2A C2A C3A 116.22(19) . . ? O2A C2A C1A 122.8(2) . . ? C3A C2A C1A 120.9(2) . . ? C2A O2A H2A 109.5 . . ? C2A C3A C4A 119.5(2) . . ? C2A C3A H3A 120.3 . . ? C4A C3A H3A 120.3 . . ? O4A C4A C3A 116.33(19) . . ? O4A C4A C5A 123.1(2) . . ? C3A C4A C5A 120.6(2) . . ? C4A O4A H4A 109.5 . . ? C6A C5A C4A 119.0(2) . . ? C6A C5A H5A 120.5 . . ? C4A C5A H5A 120.5 . . ? C5A C6A C1A 121.4(2) . . ? C5A C6A H6A 119.3 . . ? C1A C6A H6A 119.3 . . ? C16A C11A C12A 120.5(2) . . ? C16A C11A Se1A 115.40(18) . . ? C12A C11A Se1A 124.06(18) . . ? C11A C12A C13A 118.9(2) . . ? C11A C12A H12A 120.6 . . ? C13A C12A H12A 120.6 . . ? C14A C13A C12A 120.6(2) . . ? C14A C13A H13A 119.7 . . ? C12A C13A H13A 119.7 . . ? C15A C14A C13A 119.8(2) . . ? C15A C14A H14A 120.1 . . ? C13A C14A H14A 120.1 . . ? C14A C15A C16A 120.2(3) . . ? C14A C15A H15A 119.9 . . ? C16A C15A H15A 119.9 . . ? C11A C16A C15A 120.0(2) . . ? C11A C16A H16A 120.0 . . ? C15A C16A H16A 120.0 . . ? C1B Se1B C11B 101.97(9) . . ? C6B C1B C2B 118.3(2) . . ? C6B C1B Se1B 120.33(16) . . ? C2B C1B Se1B 121.12(16) . . ? O2B C2B C3B 116.57(19) . . ? O2B C2B C1B 122.8(2) . . ? C3B C2B C1B 120.6(2) . . ? C2B O2B H2B 109.5 . . ? C2B C3B C4B 120.1(2) . . ? C2B C3B H3B 119.9 . . ? C4B C3B H3B 119.9 . . ? O4B C4B C3B 116.48(19) . . ? O4B C4B C5B 123.2(2) . . ? C3B C4B C5B 120.3(2) . . ? C4B O4B H4B 109.5 . . ? C6B C5B C4B 118.9(2) . . ? C6B C5B H5B 120.5 . . ? C4B C5B H5B 120.5 . . ? C5B C6B C1B 121.8(2) . . ? C5B C6B H6B 119.1 . . ? C1B C6B H6B 119.1 . . ? C12B C11B C16B 120.3(2) . . ? C12B C11B Se1B 122.75(18) . . ? C16B C11B Se1B 116.75(18) . . ? C11B C12B C13B 119.2(2) . . ? C11B C12B H12B 120.4 . . ? C13B C12B H12B 120.4 . . ? C14B C13B C12B 120.8(2) . . ? C14B C13B H13B 119.6 . . ? C12B C13B H13B 119.6 . . ? C13B C14B C15B 119.8(2) . . ? C13B C14B H14B 120.1 . . ? C15B C14B H14B 120.1 . . ? C14B C15B C16B 120.2(2) . . ? C14B C15B H15B 119.9 . . ? C16B C15B H15B 119.9 . . ? C11B C16B C15B 119.8(2) . . ? C11B C16B H16B 120.1 . . ? C15B C16B H16B 120.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.87 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.592 _refine_diff_density_min -1.234 _refine_diff_density_rms 0.089 #===END data_8 _database_code_CSD 197549 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1-methoxy-4-methyl-2-(phenylseleno)benzene ; _chemical_name_common 8 _chemical_formula_moiety 'C14 H14 O Se' _chemical_formula_sum 'C14 H14 O Se' _chemical_formula_weight 277.21 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.991(2) _cell_length_b 9.9673(18) _cell_length_c 15.930(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2380.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 40.04 _cell_measurement_theta_max 42.24 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1120 _exptl_absorpt_coefficient_mu 4.057 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.121 _exptl_absorpt_correction_T_max 0.242 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 7.2 _diffrn_reflns_number 6064 _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_sigmaI/netI 0.0212 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 5.55 _diffrn_reflns_theta_max 74.91 _reflns_number_total 2447 _reflns_number_gt 2384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0267P)^2^+1.9116P] 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 SHELXL _refine_ls_extinction_coef 0.00204(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2447 _refine_ls_number_parameters 148 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0262 _refine_ls_wR_factor_ref 0.0727 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _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 -0.005245(13) 0.21460(2) 0.500131(10) 0.02166(10) Uani 1 1 d . . . C1 C 0.10628(12) 0.30767(16) 0.49113(10) 0.0169(3) Uani 1 1 d . . . C2 C 0.15513(11) 0.28017(15) 0.41824(10) 0.0182(3) Uani 1 1 d . . . O2 O 0.11432(8) 0.19275(12) 0.36405(7) 0.0223(3) Uani 1 1 d . . . C7 C 0.15858(13) 0.16256(19) 0.28717(11) 0.0273(4) Uani 1 1 d . . . H71 H 0.2158 0.1192 0.2992 0.033 Uiso 1 1 calc R . . H72 H 0.1690 0.2457 0.2558 0.033 Uiso 1 1 calc R . . H73 H 0.1214 0.1020 0.2537 0.033 Uiso 1 1 calc R . . C3 C 0.23733(11) 0.34022(17) 0.40556(10) 0.0211(3) Uani 1 1 d . . . H3 H 0.2712 0.3200 0.3568 0.025 Uiso 1 1 calc R . . C4 C 0.27010(11) 0.43071(17) 0.46495(11) 0.0214(3) Uani 1 1 d . . . H4 H 0.3264 0.4721 0.4559 0.026 Uiso 1 1 calc R . . C5 C 0.22203(11) 0.46146(16) 0.53703(11) 0.0199(3) Uani 1 1 d . . . C8 C 0.25519(12) 0.56462(18) 0.59901(11) 0.0263(4) Uani 1 1 d . . . H81 H 0.2371 0.5387 0.6558 0.032 Uiso 1 1 calc R . . H82 H 0.2296 0.6524 0.5853 0.032 Uiso 1 1 calc R . . H83 H 0.3204 0.5697 0.5961 0.032 Uiso 1 1 calc R . . C6 C 0.13991(11) 0.39777(15) 0.54964(10) 0.0180(3) Uani 1 1 d . . . H6 H 0.1066 0.4165 0.5990 0.022 Uiso 1 1 calc R . . C11 C -0.03732(10) 0.26125(16) 0.61312(10) 0.0177(3) Uani 1 1 d . . . C12 C -0.02983(11) 0.16438(17) 0.67575(11) 0.0208(3) Uani 1 1 d . . . H12 H -0.0061 0.0784 0.6629 0.025 Uiso 1 1 calc R . . C13 C -0.05718(12) 0.19396(17) 0.75706(11) 0.0232(4) Uani 1 1 d . . . H13 H -0.0520 0.1280 0.7999 0.028 Uiso 1 1 calc R . . C14 C -0.09197(11) 0.31940(18) 0.77594(10) 0.0222(3) Uani 1 1 d . . . H14 H -0.1107 0.3394 0.8315 0.027 Uiso 1 1 calc R . . C15 C -0.09922(11) 0.41537(17) 0.71337(11) 0.0214(3) Uani 1 1 d . . . H15 H -0.1225 0.5016 0.7264 0.026 Uiso 1 1 calc R . . C16 C -0.07282(11) 0.38667(16) 0.63174(10) 0.0201(3) Uani 1 1 d . . . H16 H -0.0790 0.4523 0.5889 0.024 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 0.02168(14) 0.02552(15) 0.01776(15) -0.00395(6) 0.00216(6) -0.00732(7) C1 0.0184(8) 0.0145(7) 0.0179(8) 0.0031(6) 0.0002(6) 0.0005(6) C2 0.0212(8) 0.0160(7) 0.0175(8) 0.0013(6) -0.0017(6) 0.0037(6) O2 0.0214(6) 0.0273(6) 0.0183(6) -0.0051(5) 0.0016(5) -0.0005(5) C7 0.0304(9) 0.0307(9) 0.0207(8) -0.0067(7) 0.0055(7) 0.0007(7) C3 0.0205(8) 0.0220(8) 0.0208(8) 0.0016(6) 0.0031(6) 0.0045(6) C4 0.0171(8) 0.0197(8) 0.0274(9) 0.0040(7) 0.0018(6) -0.0006(6) C5 0.0208(8) 0.0171(7) 0.0220(8) 0.0031(6) -0.0024(6) 0.0002(6) C8 0.0265(9) 0.0245(8) 0.0279(9) -0.0011(7) -0.0003(7) -0.0070(7) C6 0.0215(8) 0.0164(7) 0.0161(7) 0.0022(6) 0.0003(6) 0.0003(6) C11 0.0165(7) 0.0197(7) 0.0170(7) 0.0006(6) -0.0001(6) -0.0040(6) C12 0.0198(8) 0.0188(8) 0.0238(8) 0.0020(6) -0.0011(7) 0.0007(6) C13 0.0253(9) 0.0233(8) 0.0209(8) 0.0066(7) -0.0012(7) -0.0018(7) C14 0.0222(8) 0.0277(8) 0.0166(8) -0.0009(6) -0.0003(6) -0.0026(7) C15 0.0215(8) 0.0191(8) 0.0237(8) -0.0018(6) -0.0023(7) 0.0002(6) C16 0.0216(8) 0.0185(7) 0.0202(8) 0.0042(6) -0.0016(6) -0.0020(6) _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 1.9174(18) . ? Se1 C11 1.9203(16) . ? C1 C6 1.389(2) . ? C1 C2 1.400(2) . ? C2 O2 1.371(2) . ? C2 C3 1.385(2) . ? O2 C7 1.425(2) . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C3 C4 1.396(2) . ? C3 H3 0.9500 . ? C4 C5 1.390(3) . ? C4 H4 0.9500 . ? C5 C6 1.400(2) . ? C5 C8 1.510(2) . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? C6 H6 0.9500 . ? C11 C16 1.391(2) . ? C11 C12 1.393(2) . ? C12 C13 1.390(2) . ? C12 H12 0.9500 . ? C13 C14 1.388(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 C16 1.389(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C11 99.87(7) . . ? C6 C1 C2 119.56(16) . . ? C6 C1 Se1 125.38(12) . . ? C2 C1 Se1 115.05(12) . . ? O2 C2 C3 125.45(15) . . ? O2 C2 C1 114.42(15) . . ? C3 C2 C1 120.12(15) . . ? C2 O2 C7 117.89(13) . . ? O2 C7 H71 109.5 . . ? O2 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? O2 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? C2 C3 C4 119.57(15) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 121.32(16) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 118.33(16) . . ? C4 C5 C8 121.32(16) . . ? C6 C5 C8 120.31(15) . . ? C5 C8 H81 109.5 . . ? C5 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C5 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? C1 C6 C5 121.08(15) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C16 C11 C12 120.08(15) . . ? C16 C11 Se1 120.89(12) . . ? C12 C11 Se1 118.90(12) . . ? C13 C12 C11 119.78(16) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C14 C13 C12 120.25(15) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 119.70(16) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C14 C15 C16 120.59(16) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.59(15) . . ? C15 C16 H16 120.2 . . ? C11 C16 H16 120.2 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 74.91 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.504 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.059 #===END data_9 _database_code_CSD 197550 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,5-dimethyl-4-(phenylseleno)phenol ; _chemical_name_common 9 _chemical_formula_moiety 'C14 H14 O Se' _chemical_formula_sum 'C14 H14 O Se' _chemical_formula_weight 277.21 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 9.0416(12) _cell_length_b 7.8911(10) _cell_length_c 17.6103(18) _cell_angle_alpha 90.00 _cell_angle_beta 102.406(10) _cell_angle_gamma 90.00 _cell_volume 1227.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 122.0(5) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 39.46 _cell_measurement_theta_max 41.77 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 3.035 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.083 _exptl_absorpt_correction_T_max 0.180 _exptl_absorpt_process_details '(DeTitta, 1985)' _diffrn_ambient_temperature 122.0(5) _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 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 5 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 167 _diffrn_standards_decay_% 'no decay' _diffrn_reflns_number 9405 _diffrn_reflns_av_R_equivalents 0.0501 _diffrn_reflns_av_sigmaI/netI 0.0106 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 26.43 _reflns_number_total 2520 _reflns_number_gt 2473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (1994)' _computing_cell_refinement 'CAD4 Express (1994)' _computing_data_reduction 'DREADD (Blessing 1987)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _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^)+(0.0422P)^2^+1.4564P] 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 SHELXL _refine_ls_extinction_coef 0.0075(8) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2520 _refine_ls_number_parameters 149 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0268 _refine_ls_R_factor_gt 0.0265 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0758 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.17703(2) 0.04582(3) 0.059285(12) 0.01987(11) Uani 1 1 d . . . C1 C 0.1213(2) 0.2687(2) 0.08691(11) 0.0143(4) Uani 1 1 d . . . C2 C 0.1955(2) 0.4127(3) 0.06733(11) 0.0140(4) Uani 1 1 d . . . C3 C 0.1428(2) 0.5698(3) 0.08559(12) 0.0149(4) Uani 1 1 d . . . H3 H 0.1911 0.6695 0.0729 0.018 Uiso 1 1 calc R . . C4 C 0.0212(2) 0.5847(3) 0.12184(12) 0.0158(4) Uani 1 1 d . . . O4 O -0.02977(18) 0.73990(19) 0.14021(10) 0.0221(3) Uani 1 1 d . . . H4 H 0.0189 0.8167 0.1233 0.033 Uiso 1 1 calc R . . C5 C -0.0523(2) 0.4417(3) 0.14232(12) 0.0172(4) Uani 1 1 d . . . C6 C 0.0002(2) 0.2844(3) 0.12394(12) 0.0172(4) Uani 1 1 d . . . H6 H -0.0479 0.1848 0.1370 0.021 Uiso 1 1 calc R . . C7 C 0.3295(2) 0.4046(3) 0.02945(13) 0.0204(4) Uani 1 1 d . . . H71 H 0.3482 0.5171 0.0099 0.025 Uiso 1 1 calc R . . H72 H 0.3084 0.3241 -0.0139 0.025 Uiso 1 1 calc R . . H73 H 0.4190 0.3672 0.0676 0.025 Uiso 1 1 calc R . . C8 C -0.1794(3) 0.4589(3) 0.18446(15) 0.0269(5) Uani 1 1 d . . . H81 H -0.2140 0.3460 0.1961 0.032 Uiso 1 1 calc R . . H82 H -0.2635 0.5207 0.1517 0.032 Uiso 1 1 calc R . . H83 H -0.1437 0.5212 0.2331 0.032 Uiso 1 1 calc R . . C11 C 0.3774(2) 0.0288(2) 0.12302(12) 0.0140(4) Uani 1 1 d . . . C12 C 0.4833(2) -0.0697(3) 0.09607(12) 0.0184(4) Uani 1 1 d . . . H12 H 0.4560 -0.1259 0.0473 0.022 Uiso 1 1 calc R . . C13 C 0.6292(2) -0.0853(3) 0.14114(13) 0.0222(4) Uani 1 1 d . . . H13 H 0.7015 -0.1531 0.1232 0.027 Uiso 1 1 calc R . . C14 C 0.6700(2) -0.0028(3) 0.21186(13) 0.0218(4) Uani 1 1 d . . . H14 H 0.7699 -0.0135 0.2422 0.026 Uiso 1 1 calc R . . C15 C 0.5640(2) 0.0960(3) 0.23837(12) 0.0219(4) Uani 1 1 d . . . H15 H 0.5919 0.1528 0.2869 0.026 Uiso 1 1 calc R . . C16 C 0.4178(2) 0.1118(3) 0.19420(12) 0.0179(4) Uani 1 1 d . . . H16 H 0.3456 0.1791 0.2125 0.022 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 0.01514(14) 0.01310(14) 0.02892(15) -0.00243(7) -0.00069(9) 0.00123(7) C1 0.0110(8) 0.0105(9) 0.0201(9) 0.0012(7) 0.0007(7) 0.0019(7) C2 0.0105(8) 0.0132(9) 0.0176(9) 0.0011(7) 0.0015(7) 0.0006(7) C3 0.0129(9) 0.0120(9) 0.0194(9) 0.0017(7) 0.0025(7) 0.0000(7) C4 0.0141(9) 0.0136(9) 0.0185(9) 0.0002(7) 0.0011(7) 0.0045(8) O4 0.0215(8) 0.0131(7) 0.0338(8) -0.0010(6) 0.0109(6) 0.0059(6) C5 0.0112(9) 0.0194(11) 0.0215(10) 0.0042(8) 0.0046(8) 0.0035(7) C6 0.0125(9) 0.0155(10) 0.0230(10) 0.0048(8) 0.0028(7) -0.0009(7) C7 0.0171(10) 0.0179(10) 0.0288(10) 0.0007(8) 0.0106(8) 0.0017(8) C8 0.0220(11) 0.0269(12) 0.0367(13) 0.0068(9) 0.0172(10) 0.0063(9) C11 0.0119(9) 0.0107(9) 0.0193(9) 0.0026(7) 0.0031(7) 0.0005(7) C12 0.0188(10) 0.0167(10) 0.0201(9) -0.0019(8) 0.0053(8) 0.0026(8) C13 0.0170(10) 0.0211(10) 0.0295(11) 0.0013(9) 0.0072(8) 0.0077(8) C14 0.0148(10) 0.0208(10) 0.0274(11) 0.0053(9) -0.0012(8) 0.0013(9) C15 0.0217(11) 0.0227(11) 0.0202(10) -0.0010(8) 0.0020(8) -0.0009(9) C16 0.0176(9) 0.0162(10) 0.0206(9) -0.0017(8) 0.0057(8) 0.0022(8) _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 C11 1.920(2) . ? Se1 C1 1.921(2) . ? C1 C6 1.395(3) . ? C1 C2 1.400(3) . ? C2 C3 1.390(3) . ? C2 C7 1.505(3) . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 O4 1.371(2) . ? C4 C5 1.395(3) . ? O4 H4 0.8400 . ? C5 C6 1.392(3) . ? C5 C8 1.502(3) . ? C6 H6 0.9500 . ? C7 H71 0.9800 . ? C7 H72 0.9800 . ? C7 H73 0.9800 . ? C8 H81 0.9800 . ? C8 H82 0.9800 . ? C8 H83 0.9800 . ? C11 C16 1.392(3) . ? C11 C12 1.393(3) . ? C12 C13 1.392(3) . ? C12 H12 0.9500 . ? C13 C14 1.383(3) . ? C13 H13 0.9500 . ? C14 C15 1.391(3) . ? C14 H14 0.9500 . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? 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 C11 Se1 C1 100.48(8) . . ? C6 C1 C2 120.57(18) . . ? C6 C1 Se1 118.36(15) . . ? C2 C1 Se1 121.01(14) . . ? C3 C2 C1 117.43(17) . . ? C3 C2 C7 119.30(18) . . ? C1 C2 C7 123.26(19) . . ? C2 C3 C4 121.74(18) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? O4 C4 C3 121.52(19) . . ? O4 C4 C5 117.29(18) . . ? C3 C4 C5 121.17(19) . . ? C4 O4 H4 109.5 . . ? C6 C5 C4 117.13(18) . . ? C6 C5 C8 122.06(19) . . ? C4 C5 C8 120.78(19) . . ? C5 C6 C1 121.96(19) . . ? C5 C6 H6 119.0 . . ? C1 C6 H6 119.0 . . ? C2 C7 H71 109.5 . . ? C2 C7 H72 109.5 . . ? H71 C7 H72 109.5 . . ? C2 C7 H73 109.5 . . ? H71 C7 H73 109.5 . . ? H72 C7 H73 109.5 . . ? C5 C8 H81 109.5 . . ? C5 C8 H82 109.5 . . ? H81 C8 H82 109.5 . . ? C5 C8 H83 109.5 . . ? H81 C8 H83 109.5 . . ? H82 C8 H83 109.5 . . ? C16 C11 C12 120.21(19) . . ? C16 C11 Se1 121.70(15) . . ? C12 C11 Se1 118.09(16) . . ? C13 C12 C11 119.4(2) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C12 120.6(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.8(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 119.74(19) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.43 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.395 _refine_diff_density_min -0.600 _refine_diff_density_rms 0.074 #===END