# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'J Woollins' _publ_contact_author_email JDW3@ST-ANDREWS.AC.UK _publ_section_title ; Synthesis of Novel 2,5-Diarylselenophenes from Selenation of 1,4-Diarylbutane-1,4-diones or Methanol/Arylacetylenes ; loop_ _publ_author_name 'J Woollins' 'John B. Henry' 'Guoxiong Hua.' 'Yang Li.' 'A Mount' 'Alexandra Slawin' # Attachment '2b.cif' data_pbca _database_code_depnum_ccdc_archive 'CCDC 657441' #TrackingRef '2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 Se1' _chemical_formula_sum 'C18 H16 Se1' _chemical_formula_weight 311.27 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 14.556(2) _cell_length_b 5.8313(9) _cell_length_c 33.051(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2805.4(7) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6532 _cell_measurement_theta_min 1.8643 _cell_measurement_theta_max 28.7241 _exptl_crystal_description Platelet _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 2.660 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5561 _exptl_absorpt_correction_T_max 0.9739 _exptl_absorpt_process_details 'CrystalClear (Rigaku 2004)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method dtprofit.ref _diffrn_detector_area_resol_mean 0.83 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16322 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 28.12 _reflns_number_total 3107 _reflns_number_gt 2254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0673P)^2^+0.5455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0032(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3107 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0821 _refine_ls_R_factor_gt 0.0560 _refine_ls_wR_factor_ref 0.1478 _refine_ls_wR_factor_gt 0.1337 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _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 0.83805(3) 0.01642(7) 0.282747(11) 0.0284(2) Uani 1 1 d . . . C13 C 0.8387(2) -0.0029(6) 0.18615(13) 0.0293(9) Uani 1 1 d . . . H13 H 0.8144 -0.1158 0.2039 0.035 Uiso 1 1 calc R . . C6 C 0.8378(2) -0.0817(7) 0.37768(11) 0.0313(9) Uani 1 1 d . . . H6 H 0.8132 -0.1767 0.3570 0.038 Uiso 1 1 calc R . . C7 C 0.8343(2) -0.1566(7) 0.41730(11) 0.0350(9) Uani 1 1 d . . . H7 H 0.8073 -0.3009 0.4233 0.042 Uiso 1 1 calc R . . C5 C 0.8762(3) 0.1286(6) 0.36706(10) 0.0294(8) Uani 1 1 d . . . C15 C 0.8734(3) 0.1161(7) 0.11795(11) 0.0349(9) Uani 1 1 d . . . C16 C 0.9094(3) 0.3197(6) 0.13366(10) 0.0339(9) Uani 1 1 d . . . H16 H 0.9339 0.4311 0.1157 0.041 Uiso 1 1 calc R . . C12 C 0.8751(3) 0.2009(6) 0.20194(10) 0.0280(8) Uani 1 1 d . . . C14 C 0.8381(2) -0.0400(7) 0.14528(12) 0.0320(9) Uani 1 1 d . . . H14 H 0.8123 -0.1786 0.1353 0.038 Uiso 1 1 calc R . . C11 C 0.8647(3) -0.1025(8) 0.49176(11) 0.0500(11) Uani 1 1 d . . . H11A H 0.9176 -0.0442 0.5069 0.075 Uiso 1 1 calc R . . H11B H 0.8649 -0.2706 0.4924 0.075 Uiso 1 1 calc R . . H11C H 0.8078 -0.0456 0.5041 0.075 Uiso 1 1 calc R . . C10 C 0.9116(3) 0.2640(6) 0.39847(10) 0.0345(9) Uani 1 1 d . . . H10 H 0.9382 0.4087 0.3924 0.041 Uiso 1 1 calc R . . C8 C 0.8702(3) -0.0218(6) 0.44874(12) 0.0351(9) Uani 1 1 d . . . C4 C 0.8803(3) 0.2390(6) 0.24608(10) 0.0287(8) Uani 1 1 d . . . C9 C 0.9082(3) 0.1886(7) 0.43837(10) 0.0373(9) Uani 1 1 d . . . H9 H 0.9326 0.2836 0.4591 0.045 Uiso 1 1 calc R . . C2 C 0.9179(3) 0.4029(6) 0.30904(11) 0.0306(8) Uani 1 1 d . . . H2 H 0.9421 0.5206 0.3258 0.037 Uiso 1 1 calc R . . C3 C 0.9171(3) 0.4205(6) 0.26650(11) 0.0306(8) Uani 1 1 d . . . H3 H 0.9409 0.5510 0.2528 0.037 Uiso 1 1 calc R . . C1 C 0.8813(3) 0.2050(6) 0.32464(10) 0.0290(8) Uani 1 1 d . . . C17 C 0.9103(3) 0.3624(6) 0.17452(10) 0.0344(9) Uani 1 1 d . . . H17 H 0.9349 0.5026 0.1843 0.041 Uiso 1 1 calc R . . C18 C 0.8714(3) 0.0714(8) 0.07301(11) 0.0461(11) Uani 1 1 d . . . H18A H 0.8722 -0.0944 0.0681 0.069 Uiso 1 1 calc R . . H18B H 0.9253 0.1420 0.0603 0.069 Uiso 1 1 calc R . . H18C H 0.8154 0.1374 0.0614 0.069 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 0.0262(3) 0.0202(3) 0.0388(3) -0.00082(12) -0.00005(13) -0.00307(14) C13 0.022(2) 0.024(2) 0.042(3) 0.0006(13) 0.0035(14) 0.0018(15) C6 0.027(2) 0.029(2) 0.038(2) -0.0034(16) -0.0010(14) 0.0009(16) C7 0.030(3) 0.0231(19) 0.052(2) 0.0014(16) 0.0053(15) 0.0002(16) C5 0.021(2) 0.0236(19) 0.044(2) -0.0056(14) 0.0002(15) 0.0032(16) C15 0.025(2) 0.034(2) 0.046(2) 0.0021(16) -0.0040(16) 0.0054(19) C16 0.030(2) 0.030(2) 0.042(2) 0.0043(15) 0.0016(15) 0.0015(18) C12 0.022(2) 0.0214(18) 0.0404(19) -0.0030(14) 0.0031(15) 0.0035(16) C14 0.029(3) 0.028(2) 0.039(2) 0.0013(15) -0.0038(14) 0.0008(15) C11 0.053(3) 0.046(3) 0.051(3) 0.008(2) -0.003(2) -0.002(2) C10 0.029(2) 0.0246(19) 0.050(2) 0.0007(15) -0.0030(16) -0.0021(17) C8 0.032(2) 0.032(2) 0.041(2) -0.0003(15) -0.0021(17) 0.0010(19) C4 0.018(2) 0.0216(18) 0.046(2) 0.0001(14) 0.0033(14) 0.0008(16) C9 0.035(3) 0.031(2) 0.046(2) -0.0073(16) -0.0052(16) 0.0009(18) C2 0.022(2) 0.0220(17) 0.048(2) -0.0051(14) -0.0008(15) 0.0004(16) C3 0.022(2) 0.0207(18) 0.049(2) 0.0005(15) 0.0051(16) 0.0007(16) C1 0.020(2) 0.0225(18) 0.044(2) -0.0030(14) 0.0010(14) 0.0011(16) C17 0.027(2) 0.0225(19) 0.054(2) 0.0027(15) 0.0004(16) 0.0011(17) C18 0.048(3) 0.048(3) 0.043(2) 0.0030(19) -0.0087(19) 0.001(2) _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 1.877(3) . ? Se1 C4 1.879(3) . ? C13 C14 1.368(6) . ? C13 C12 1.402(5) . ? C13 H13 0.9500 . ? C6 C7 1.381(5) . ? C6 C5 1.393(5) . ? C6 H6 0.9500 . ? C7 C8 1.404(5) . ? C7 H7 0.9500 . ? C5 C10 1.403(5) . ? C5 C1 1.473(5) . ? C15 C14 1.381(5) . ? C15 C16 1.398(5) . ? C15 C18 1.508(5) . ? C16 C17 1.373(5) . ? C16 H16 0.9500 . ? C12 C17 1.403(5) . ? C12 C4 1.478(5) . ? C14 H14 0.9500 . ? C11 C8 1.500(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C10 C9 1.391(5) . ? C10 H10 0.9500 . ? C8 C9 1.389(5) . ? C4 C3 1.365(5) . ? C9 H9 0.9500 . ? C2 C1 1.372(5) . ? C2 C3 1.410(5) . ? C2 H2 0.9500 . ? C3 H3 0.9500 . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 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 C4 87.78(16) . . ? C14 C13 C12 120.3(3) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C7 C6 C5 122.2(3) . . ? C7 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? C6 C7 C8 120.7(4) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C6 C5 C10 117.2(3) . . ? C6 C5 C1 121.8(3) . . ? C10 C5 C1 121.0(3) . . ? C14 C15 C16 117.2(3) . . ? C14 C15 C18 121.5(4) . . ? C16 C15 C18 121.3(4) . . ? C17 C16 C15 121.5(3) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C13 C12 C17 117.8(3) . . ? C13 C12 C4 120.9(3) . . ? C17 C12 C4 121.2(3) . . ? C13 C14 C15 122.6(4) . . ? C13 C14 H14 118.7 . . ? C15 C14 H14 118.7 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C10 C5 120.7(4) . . ? C9 C10 H10 119.6 . . ? C5 C10 H10 119.6 . . ? C9 C8 C7 117.4(3) . . ? C9 C8 C11 122.2(4) . . ? C7 C8 C11 120.4(4) . . ? C3 C4 C12 128.6(3) . . ? C3 C4 Se1 110.2(3) . . ? C12 C4 Se1 121.1(2) . . ? C8 C9 C10 121.8(3) . . ? C8 C9 H9 119.1 . . ? C10 C9 H9 119.1 . . ? C1 C2 C3 115.7(3) . . ? C1 C2 H2 122.2 . . ? C3 C2 H2 122.2 . . ? C4 C3 C2 116.1(3) . . ? C4 C3 H3 122.0 . . ? C2 C3 H3 122.0 . . ? C2 C1 C5 129.2(3) . . ? C2 C1 Se1 110.2(2) . . ? C5 C1 Se1 120.5(3) . . ? C16 C17 C12 120.7(3) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C6 C7 C8 -0.3(6) . . . . ? C7 C6 C5 C10 -0.1(6) . . . . ? C7 C6 C5 C1 178.7(3) . . . . ? C14 C15 C16 C17 0.4(6) . . . . ? C18 C15 C16 C17 179.1(4) . . . . ? C14 C13 C12 C17 0.0(5) . . . . ? C14 C13 C12 C4 -177.2(3) . . . . ? C12 C13 C14 C15 0.8(5) . . . . ? C16 C15 C14 C13 -1.0(6) . . . . ? C18 C15 C14 C13 -179.7(4) . . . . ? C6 C5 C10 C9 0.2(6) . . . . ? C1 C5 C10 C9 -178.7(3) . . . . ? C6 C7 C8 C9 0.5(6) . . . . ? C6 C7 C8 C11 178.9(4) . . . . ? C13 C12 C4 C3 176.6(4) . . . . ? C17 C12 C4 C3 -0.4(6) . . . . ? C13 C12 C4 Se1 -0.1(5) . . . . ? C17 C12 C4 Se1 -177.2(3) . . . . ? C1 Se1 C4 C3 -1.6(3) . . . . ? C1 Se1 C4 C12 175.7(3) . . . . ? C7 C8 C9 C10 -0.5(6) . . . . ? C11 C8 C9 C10 -178.8(4) . . . . ? C5 C10 C9 C8 0.1(6) . . . . ? C12 C4 C3 C2 -175.8(3) . . . . ? Se1 C4 C3 C2 1.3(4) . . . . ? C1 C2 C3 C4 0.0(5) . . . . ? C3 C2 C1 C5 176.4(4) . . . . ? C3 C2 C1 Se1 -1.3(4) . . . . ? C6 C5 C1 C2 -178.8(4) . . . . ? C10 C5 C1 C2 0.0(6) . . . . ? C6 C5 C1 Se1 -1.4(5) . . . . ? C10 C5 C1 Se1 177.4(3) . . . . ? C4 Se1 C1 C2 1.6(3) . . . . ? C4 Se1 C1 C5 -176.3(3) . . . . ? C15 C16 C17 C12 0.4(6) . . . . ? C13 C12 C17 C16 -0.5(6) . . . . ? C4 C12 C17 C16 176.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.857 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.858 _refine_diff_density_min -0.940 _refine_diff_density_rms 0.116