# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2002 data_cy11se _database_code_CSD 184423 _journal_coden_Cambridge 207 loop_ _publ_author_name 'Helmut Poleschner' 'Konrad Seppelt' _publ_contact_author_name 'Dr Helmut Poleschner' _publ_contact_author_address ; Institut fur Chemie, Anorganische and Analytische Chemie Freie Universitat Berlin Fabeckstrasse 34-36 Berlin D-14195 GERMANY ; _publ_contact_author_email 'HPOL@CHEMIE.FU-BERLIN.DE' _publ_requested_journal 'Perkin Transactions 1' _publ_section_title ; PhSeOTf/Et3N3HF and PhSeSbF6/Et3N3HF as new PhSe-F equivalents in fluoroselenenylation of acetylenes ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; '(E)-1-Fluoro-2-phenylseleno-cycloundecene' ; _chemical_name_common '(E)-1-Fluoro-2-phenylseleno-cycloundecene' _chemical_melting_point '52.5 - 53.3 C' _chemical_formula_moiety ? _chemical_formula_sum 'C17 H23 F Se' _chemical_formula_weight 325.31 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Se' 'Se' -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.0991(15) _cell_length_b 6.3581(14) _cell_length_c 16.766(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.415(5) _cell_angle_gamma 90.00 _cell_volume 756.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 2.477 _exptl_absorpt_correction_type semiempirical _exptl_absorpt_correction_T_min 0.621 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Equilibration of symmetry equivalent reflections' _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart CCD 1000 TM' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9687 _diffrn_reflns_av_R_equivalents 0.0459 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.21 _diffrn_reflns_theta_max 30.93 _reflns_number_total 4699 _reflns_number_gt 4447 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1146P)^2^+0.8778P] 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 0.003(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.10(2) _refine_ls_number_reflns 4699 _refine_ls_number_parameters 175 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1789 _refine_ls_wR_factor_gt 0.1738 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.65347(6) 0.68986(10) -0.17912(2) 0.03132(16) Uani 1 1 d . . . F F 1.0751(6) 1.0368(7) -0.2743(3) 0.0483(9) Uani 1 1 d . . . C1 C 0.7128(5) 0.7264(6) -0.0689(2) 0.0224(8) Uani 1 1 d . . . C2 C 0.8119(6) 0.8955(8) -0.0407(3) 0.0290(9) Uani 1 1 d . . . H2 H 0.8553 1.0011 -0.0762 0.074(6) Uiso 1 1 calc R . . C3 C 0.8485(7) 0.9107(10) 0.0411(3) 0.0334(10) Uani 1 1 d . . . H3 H 0.9180 1.0269 0.0615 0.074(6) Uiso 1 1 calc R . . C4 C 0.7842(7) 0.7582(10) 0.0924(3) 0.0351(11) Uani 1 1 d . . . H4 H 0.8097 0.7691 0.1479 0.074(6) Uiso 1 1 calc R . . C5 C 0.6841(7) 0.5915(9) 0.0636(3) 0.0319(10) Uani 1 1 d . . . H5 H 0.6382 0.4881 0.0995 0.074(6) Uiso 1 1 calc R . . C6 C 0.6483(6) 0.5712(8) -0.0174(3) 0.0286(8) Uani 1 1 d . . . H6 H 0.5809 0.4532 -0.0374 0.074(6) Uiso 1 1 calc R . . C16 C 1.0862(7) 0.6845(17) -0.2382(5) 0.064(2) Uani 1 1 d . . . H16A H 1.0176 0.5766 -0.2073 0.074(6) Uiso 1 1 calc R . . H16B H 1.2071 0.7137 -0.2105 0.074(6) Uiso 1 1 calc R . . C12 C 0.7580(14) 0.750(3) -0.4618(4) 0.114(7) Uani 1 1 d . . . H12A H 0.7181 0.6055 -0.4764 0.074(6) Uiso 1 1 calc R . . H12B H 0.7604 0.8337 -0.5114 0.074(6) Uiso 1 1 calc R . . C13 C 0.9421(14) 0.7392(16) -0.4312(4) 0.071(3) Uani 1 1 d . . . H13A H 0.9728 0.8717 -0.4029 0.074(6) Uiso 1 1 calc R . . H13B H 1.0322 0.7221 -0.4755 0.074(6) Uiso 1 1 calc R . . C17 C 0.9742(9) 0.8768(10) -0.2429(3) 0.0401(12) Uani 1 1 d . . . C7 C 0.8042(9) 0.9080(10) -0.2235(3) 0.0389(12) Uani 1 1 d . . . C14 C 0.9602(19) 0.5583(14) -0.3750(5) 0.088(4) Uani 1 1 d . . . H14A H 0.8460 0.5460 -0.3417 0.074(6) Uiso 1 1 calc R . . H14B H 0.9769 0.4253 -0.4048 0.074(6) Uiso 1 1 calc R . . C9 C 0.5619(12) 1.1312(15) -0.2976(9) 0.097(5) Uani 1 1 d . . . H9A H 0.5097 1.2755 -0.2999 0.074(6) Uiso 1 1 calc R . . H9B H 0.4585 1.0347 -0.2828 0.074(6) Uiso 1 1 calc R . . C11 C 0.5922(16) 0.854(2) -0.4010(5) 0.086(4) Uani 1 1 d . . . H11A H 0.4676 0.8472 -0.4277 0.074(6) Uiso 1 1 calc R . . H11B H 0.5854 0.7697 -0.3513 0.074(6) Uiso 1 1 calc R . . C15 C 1.1251(16) 0.6006(18) -0.3251(9) 0.113(6) Uani 1 1 d . . . H15A H 1.2046 0.7051 -0.3529 0.074(6) Uiso 1 1 calc R . . H15B H 1.1993 0.4692 -0.3206 0.074(6) Uiso 1 1 calc R . . C10 C 0.6368(15) 1.069(2) -0.3816(7) 0.086(4) Uani 1 1 d . . . H10A H 0.5801 1.1634 -0.4223 0.074(6) Uiso 1 1 calc R . . H10B H 0.7751 1.0890 -0.3828 0.074(6) Uiso 1 1 calc R . . C8 C 0.7097(13) 1.1225(13) -0.2359(7) 0.067(2) Uani 1 1 d . . . H8A H 0.6542 1.1673 -0.1847 0.074(6) Uiso 1 1 calc R . . H8B H 0.8084 1.2261 -0.2497 0.074(6) 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 0.0365(2) 0.0333(2) 0.0243(2) -0.0059(2) 0.00613(13) -0.0146(2) F 0.0501(19) 0.047(2) 0.048(2) 0.0024(18) 0.0074(16) -0.0105(17) C1 0.0216(13) 0.022(3) 0.0237(15) -0.0007(13) 0.0043(11) -0.0034(13) C2 0.0299(19) 0.030(2) 0.0268(19) -0.0035(17) 0.0038(15) -0.0117(17) C3 0.031(2) 0.040(3) 0.028(2) -0.002(2) -0.0006(16) -0.0113(19) C4 0.0285(19) 0.050(3) 0.0270(19) 0.0015(19) -0.0044(15) -0.0038(19) C5 0.0271(19) 0.035(3) 0.034(2) 0.0054(19) 0.0014(17) -0.0014(18) C6 0.0285(18) 0.030(2) 0.0278(19) 0.0023(17) 0.0029(15) -0.0060(16) C16 0.032(2) 0.084(5) 0.076(4) 0.053(5) -0.018(2) -0.023(3) C12 0.108(6) 0.214(18) 0.019(2) 0.032(5) -0.012(3) -0.107(10) C13 0.101(6) 0.077(8) 0.035(3) -0.006(3) 0.020(3) -0.036(5) C17 0.050(3) 0.036(3) 0.035(2) -0.001(2) 0.010(2) -0.008(2) C7 0.049(3) 0.041(3) 0.027(2) -0.006(2) 0.0032(19) -0.017(2) C14 0.165(11) 0.043(4) 0.055(4) -0.020(4) 0.067(6) -0.033(6) C9 0.043(3) 0.042(4) 0.207(15) 0.009(6) 0.031(6) 0.007(3) C11 0.104(7) 0.111(9) 0.043(4) 0.035(5) -0.027(4) -0.070(7) C15 0.092(7) 0.079(7) 0.169(12) -0.073(8) 0.102(8) -0.048(6) C10 0.073(5) 0.094(8) 0.090(7) 0.060(7) -0.025(5) -0.018(5) C8 0.067(4) 0.037(3) 0.097(7) 0.013(4) 0.025(4) -0.002(3) _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 C7 1.906(6) . ? Se1 C1 1.907(4) . ? F C17 1.353(7) . ? C1 C2 1.367(6) . ? C1 C6 1.391(6) . ? C2 C3 1.398(7) . ? C2 H2 0.9500 . ? C3 C4 1.376(8) . ? C3 H3 0.9500 . ? C4 C5 1.362(8) . ? C4 H4 0.9500 . ? C5 C6 1.386(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C16 C17 1.460(12) . ? C16 C15 1.578(15) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C12 C13 1.402(14) . ? C12 C11 1.696(19) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.492(14) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C17 C7 1.268(9) . ? C7 C8 1.534(11) . ? C14 C15 1.459(19) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C9 C8 1.468(17) . ? C9 C10 1.560(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 C10 1.445(17) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? 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 C7 Se1 C1 99.71(19) . . ? C2 C1 C6 120.9(4) . . ? C2 C1 Se1 122.8(3) . . ? C6 C1 Se1 116.3(3) . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.1(5) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 120.7(5) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C5 C6 C1 118.9(4) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C17 C16 C15 109.4(8) . . ? C17 C16 H16A 109.8 . . ? C15 C16 H16A 109.8 . . ? C17 C16 H16B 109.8 . . ? C15 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? C13 C12 C11 116.6(7) . . ? C13 C12 H12A 108.1 . . ? C11 C12 H12A 108.1 . . ? C13 C12 H12B 108.1 . . ? C11 C12 H12B 108.1 . . ? H12A C12 H12B 107.3 . . ? C12 C13 C14 110.1(9) . . ? C12 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? C12 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.2 . . ? C7 C17 F 119.4(6) . . ? C7 C17 C16 129.5(6) . . ? F C17 C16 111.1(5) . . ? C17 C7 C8 121.3(6) . . ? C17 C7 Se1 121.6(6) . . ? C8 C7 Se1 117.0(5) . . ? C15 C14 C13 106.6(9) . . ? C15 C14 H14A 110.4 . . ? C13 C14 H14A 110.4 . . ? C15 C14 H14B 110.4 . . ? C13 C14 H14B 110.4 . . ? H14A C14 H14B 108.6 . . ? C8 C9 C10 112.3(7) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C10 C11 C12 110.7(9) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C14 C15 C16 116.5(6) . . ? C14 C15 H15A 108.2 . . ? C16 C15 H15A 108.2 . . ? C14 C15 H15B 108.2 . . ? C16 C15 H15B 108.2 . . ? H15A C15 H15B 107.3 . . ? C11 C10 C9 111.5(8) . . ? C11 C10 H10A 109.3 . . ? C9 C10 H10A 109.3 . . ? C11 C10 H10B 109.3 . . ? C9 C10 H10B 109.3 . . ? H10A C10 H10B 108.0 . . ? C9 C8 C7 116.0(8) . . ? C9 C8 H8A 108.3 . . ? C7 C8 H8A 108.3 . . ? C9 C8 H8B 108.3 . . ? C7 C8 H8B 108.3 . . ? H8A C8 H8B 107.4 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 30.93 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.753 _refine_diff_density_min -1.145 _refine_diff_density_rms 0.156