# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Liu, Rai-Shung' _publ_contact_author_email rsliu@mx.nthu.edu.tw _publ_section_title ; Platinum-Catalyzed Cycloisomerization of 1,4-Enynes via Activation of a sp3-Hybridized C-H Bond ; loop_ _publ_author_name 'Rai-Shung Liu' 'Vasu Dhananjayan' # Attachment '- 090809_0m.cif' data_090809_0m _database_code_depnum_ccdc_archive 'CCDC 755454' #TrackingRef '- 090809_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H16' _chemical_formula_weight 268.34 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n 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 7.2738(2) _cell_length_b 22.9796(6) _cell_length_c 8.8198(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.426(2) _cell_angle_gamma 90.00 _cell_volume 1445.00(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3661 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Lump _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.233 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.070 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7131 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12682 _diffrn_reflns_av_R_equivalents 0.0208 _diffrn_reflns_av_sigmaI/netI 0.0181 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.42 _reflns_number_total 2942 _reflns_number_gt 2263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker APEX2' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'Shelxtl-97 (Sheldrick, 2008)' _computing_structure_refinement 'Shelxtl-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker APEX2' _computing_publication_material 'Bruker APEX2' _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^)+(0.0750P)^2^+0.1759P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2942 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1420 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 C1 C 0.9461(3) 0.05459(8) 0.1660(3) 0.0847(6) Uani 1 1 d . . . H1 H 0.9406 0.0152 0.1416 0.102 Uiso 1 1 calc R . . C2 C 0.9309(3) 0.09478(7) 0.0491(2) 0.0692(5) Uani 1 1 d . . . H2 H 0.9156 0.0830 -0.0535 0.083 Uiso 1 1 calc R . . C3 C 0.9388(2) 0.15339(6) 0.08769(18) 0.0511(4) Uani 1 1 d . . . C4 C 0.93422(19) 0.20510(6) -0.00935(17) 0.0454(4) Uani 1 1 d . . . C5 C 0.94583(18) 0.25476(6) 0.08648(15) 0.0407(3) Uani 1 1 d . . . C6 C 0.95655(18) 0.31135(6) 0.02837(15) 0.0415(3) Uani 1 1 d . . . C7 C 0.9688(2) 0.36487(6) 0.12288(15) 0.0443(3) Uani 1 1 d . . . C8 C 1.0786(2) 0.41150(7) 0.09287(18) 0.0572(4) Uani 1 1 d . . . H8 H 1.1474 0.4082 0.0149 0.069 Uiso 1 1 calc R . . C9 C 1.0870(3) 0.46237(8) 0.1767(2) 0.0709(5) Uani 1 1 d . . . H9 H 1.1608 0.4930 0.1543 0.085 Uiso 1 1 calc R . . C10 C 0.9880(3) 0.46823(8) 0.2923(2) 0.0761(6) Uani 1 1 d . . . H10 H 0.9942 0.5027 0.3485 0.091 Uiso 1 1 calc R . . C11 C 0.95634(19) 0.31326(7) -0.12985(16) 0.0474(4) Uani 1 1 d . . . C12 C 0.9420(2) 0.26486(7) -0.22385(16) 0.0506(4) Uani 1 1 d . . . C13 C 0.9301(2) 0.20942(7) -0.16907(17) 0.0535(4) Uani 1 1 d . . . H13 H 0.9200 0.1769 -0.2331 0.064 Uiso 1 1 calc R . . C14 C 0.9552(2) 0.23549(6) 0.25191(15) 0.0436(3) Uani 1 1 d . . . H14A H 1.0677 0.2501 0.3191 0.052 Uiso 1 1 calc R . . H14B H 0.8464 0.2488 0.2902 0.052 Uiso 1 1 calc R . . C15 C 0.95860(19) 0.17055(6) 0.24185(17) 0.0479(4) Uani 1 1 d . . . C16 C 0.9752(2) 0.12981(7) 0.3587(2) 0.0632(4) Uani 1 1 d . . . H16 H 0.9900 0.1412 0.4616 0.076 Uiso 1 1 calc R . . C17 C 0.9693(3) 0.07121(8) 0.3182(3) 0.0828(6) Uani 1 1 d . . . H17 H 0.9812 0.0430 0.3951 0.099 Uiso 1 1 calc R . . C18 C 0.9402(2) 0.30024(8) -0.36837(17) 0.0646(5) Uani 1 1 d . . . H18A H 0.8243 0.2974 -0.4445 0.078 Uiso 1 1 calc R . . H18B H 1.0486 0.2941 -0.4152 0.078 Uiso 1 1 calc R . . C19 C 0.9537(2) 0.35500(8) -0.26349(16) 0.0583(4) Uani 1 1 d . . . H19A H 1.0684 0.3771 -0.2574 0.070 Uiso 1 1 calc R . . H19B H 0.8441 0.3800 -0.2851 0.070 Uiso 1 1 calc R . . C20 C 0.8691(2) 0.37194(7) 0.24051(18) 0.0564(4) Uani 1 1 d . . . H20 H 0.7938 0.3417 0.2632 0.068 Uiso 1 1 calc R . . C21 C 0.8796(3) 0.42299(8) 0.3246(2) 0.0720(5) Uani 1 1 d . . . H21 H 0.8126 0.4266 0.4036 0.086 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 C1 0.0799(14) 0.0460(11) 0.1327(19) -0.0077(12) 0.0322(13) -0.0009(9) C2 0.0619(11) 0.0500(10) 0.0966(13) -0.0170(9) 0.0179(9) -0.0010(8) C3 0.0362(7) 0.0483(9) 0.0686(9) -0.0110(7) 0.0098(6) -0.0008(6) C4 0.0334(7) 0.0522(9) 0.0501(8) -0.0120(6) 0.0074(6) 0.0005(6) C5 0.0338(7) 0.0492(8) 0.0395(7) -0.0074(6) 0.0084(5) -0.0005(5) C6 0.0358(7) 0.0510(8) 0.0390(7) -0.0021(6) 0.0104(5) 0.0007(6) C7 0.0450(8) 0.0462(8) 0.0410(7) 0.0010(6) 0.0067(6) 0.0019(6) C8 0.0605(10) 0.0575(10) 0.0546(9) 0.0012(7) 0.0140(7) -0.0062(7) C9 0.0854(13) 0.0510(10) 0.0720(11) 0.0015(8) 0.0053(10) -0.0157(9) C10 0.1138(17) 0.0493(10) 0.0628(11) -0.0101(8) 0.0111(11) 0.0027(10) C11 0.0377(7) 0.0653(9) 0.0402(7) -0.0007(6) 0.0102(6) -0.0001(6) C12 0.0368(7) 0.0747(11) 0.0411(7) -0.0088(7) 0.0096(6) 0.0009(7) C13 0.0392(8) 0.0708(11) 0.0500(8) -0.0249(7) 0.0078(6) 0.0022(7) C14 0.0408(7) 0.0469(8) 0.0436(7) -0.0027(6) 0.0098(6) -0.0027(6) C15 0.0366(7) 0.0466(8) 0.0612(9) 0.0000(7) 0.0113(6) -0.0013(6) C16 0.0555(10) 0.0594(10) 0.0770(11) 0.0120(8) 0.0185(8) 0.0030(8) C17 0.0766(13) 0.0561(11) 0.1210(18) 0.0268(12) 0.0323(12) 0.0073(9) C18 0.0438(9) 0.1114(15) 0.0396(8) -0.0020(8) 0.0103(6) -0.0007(8) C19 0.0484(9) 0.0838(12) 0.0439(8) 0.0087(7) 0.0120(6) -0.0020(8) C20 0.0702(11) 0.0482(9) 0.0552(8) -0.0018(7) 0.0235(8) 0.0022(7) C21 0.1069(15) 0.0540(10) 0.0615(10) -0.0064(8) 0.0321(10) 0.0112(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 C1 C2 1.372(3) . ? C1 C17 1.373(3) . ? C1 H1 0.9300 . ? C2 C3 1.387(2) . ? C2 H2 0.9300 . ? C3 C15 1.396(2) . ? C3 C4 1.461(2) . ? C4 C13 1.407(2) . ? C4 C5 1.4127(18) . ? C5 C6 1.4054(19) . ? C5 C14 1.5134(18) . ? C6 C11 1.3959(18) . ? C6 C7 1.4786(19) . ? C7 C20 1.388(2) . ? C7 C8 1.393(2) . ? C8 C9 1.378(2) . ? C8 H8 0.9300 . ? C9 C10 1.367(3) . ? C9 H9 0.9300 . ? C10 C21 1.368(3) . ? C10 H10 0.9300 . ? C11 C12 1.379(2) . ? C11 C19 1.517(2) . ? C12 C13 1.371(2) . ? C12 C18 1.510(2) . ? C13 H13 0.9300 . ? C14 C15 1.495(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.380(2) . ? C16 C17 1.391(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.553(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.382(2) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 C2 C1 C17 121.53(18) . . ? C2 C1 H1 119.2 . . ? C17 C1 H1 119.2 . . ? C1 C2 C3 118.43(19) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C15 120.29(16) . . ? C2 C3 C4 130.62(16) . . ? C15 C3 C4 109.08(13) . . ? C13 C4 C5 121.93(14) . . ? C13 C4 C3 129.62(13) . . ? C5 C4 C3 108.36(13) . . ? C6 C5 C4 122.03(13) . . ? C6 C5 C14 128.84(12) . . ? C4 C5 C14 109.05(12) . . ? C11 C6 C5 113.86(12) . . ? C11 C6 C7 121.70(13) . . ? C5 C6 C7 124.44(12) . . ? C20 C7 C8 117.14(14) . . ? C20 C7 C6 122.45(13) . . ? C8 C7 C6 120.38(13) . . ? C9 C8 C7 121.14(16) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C10 C9 C8 120.66(17) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C9 C10 C21 119.38(16) . . ? C9 C10 H10 120.3 . . ? C21 C10 H10 120.3 . . ? C12 C11 C6 124.11(14) . . ? C12 C11 C19 93.15(12) . . ? C6 C11 C19 142.57(14) . . ? C13 C12 C11 122.68(13) . . ? C13 C12 C18 143.82(14) . . ? C11 C12 C18 93.46(13) . . ? C12 C13 C4 115.36(13) . . ? C12 C13 H13 122.3 . . ? C4 C13 H13 122.3 . . ? C15 C14 C5 103.47(11) . . ? C15 C14 H14A 111.1 . . ? C5 C14 H14A 111.1 . . ? C15 C14 H14B 111.1 . . ? C5 C14 H14B 111.1 . . ? H14A C14 H14B 109.0 . . ? C16 C15 C3 120.85(15) . . ? C16 C15 C14 129.26(14) . . ? C3 C15 C14 109.88(13) . . ? C15 C16 C17 118.12(18) . . ? C15 C16 H16 120.9 . . ? C17 C16 H16 120.9 . . ? C1 C17 C16 120.77(19) . . ? C1 C17 H17 119.6 . . ? C16 C17 H17 119.6 . . ? C12 C18 C19 86.82(11) . . ? C12 C18 H18A 114.2 . . ? C19 C18 H18A 114.2 . . ? C12 C18 H18B 114.2 . . ? C19 C18 H18B 114.2 . . ? H18A C18 H18B 111.3 . . ? C11 C19 C18 86.56(12) . . ? C11 C19 H19A 114.2 . . ? C18 C19 H19A 114.2 . . ? C11 C19 H19B 114.2 . . ? C18 C19 H19B 114.2 . . ? H19A C19 H19B 111.4 . . ? C21 C20 C7 121.24(16) . . ? C21 C20 H20 119.4 . . ? C7 C20 H20 119.4 . . ? C10 C21 C20 120.45(17) . . ? C10 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.42 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.188 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.087