# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Hsing-Jang Liu' 'Liang-Rern Kung' 'Kak-Shan Shia' 'Che-Hao Tu' _publ_contact_author_name 'Dr Hsing-Jang Liu' _publ_contact_author_address ; Department of Chemistry National Tsing Hua University Hsinchu Taiwan 30013 CHINA ; _publ_contact_author_email HJLIU@MX.NTHU.EDU.TW _publ_requested_journal 'Chemical Communications' _publ_section_title ; Palladium(II) acetate mediated oxidative cyclization of -unsaturated a-cyano ketones. A facile methylenecyclopentane annulation process ; data_ja03m _database_code_CSD 213631 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H13 N O' _chemical_formula_weight 175.22 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' N N 0.0061 0.0033 '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' _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 7.0410(8) _cell_length_b 11.3049(14) _cell_length_c 12.3768(14) _cell_angle_alpha 90.00 _cell_angle_beta 100.859(2) _cell_angle_gamma 90.00 _cell_volume 967.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 290(2) _cell_measurement_reflns_used 1270 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Columnar _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.203 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 376 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.76224 _exptl_absorpt_correction_T_max 0.96869 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 290(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6138 _diffrn_reflns_av_R_equivalents 0.0626 _diffrn_reflns_av_sigmaI/netI 0.0749 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 28.31 _reflns_number_total 2331 _reflns_number_gt 1512 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.0986P)^2^+0.4077P] where P==(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2331 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1788 _refine_ls_R_factor_gt 0.1209 _refine_ls_wR_factor_ref 0.2633 _refine_ls_wR_factor_gt 0.2372 _refine_ls_goodness_of_fit_ref 1.213 _refine_ls_restrained_S_all 1.213 _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 O1 O -0.1589(4) 0.4347(2) 0.8963(2) 0.0592(8) Uani 1 1 d . . . N1 N -0.1183(5) 0.2605(3) 1.1251(3) 0.0628(10) Uani 1 1 d . . . C1 C 0.0596(4) 0.2766(3) 0.9579(2) 0.0326(7) Uani 1 1 d . . . C2 C -0.0100(4) 0.3866(3) 0.8885(3) 0.0367(8) Uani 1 1 d . . . C3 C 0.1180(5) 0.4273(4) 0.8123(3) 0.0503(10) Uani 1 1 d . . . C4 C 0.3277(5) 0.4348(4) 0.8712(3) 0.0558(11) Uani 1 1 d . . . C5 C 0.3962(5) 0.3155(4) 0.9173(3) 0.0530(10) Uani 1 1 d . . . C6 C 0.2821(5) 0.2700(3) 1.0020(3) 0.0418(9) Uani 1 1 d . . . C7 C 0.3126(6) 0.1377(4) 1.0235(3) 0.0610(11) Uani 1 1 d . . . C8 C 0.1850(6) 0.0792(4) 0.9260(4) 0.0673(12) Uani 1 1 d . . . C9 C 0.0178(5) 0.1620(3) 0.8903(3) 0.0429(9) Uani 1 1 d . . . C10 C -0.1419(6) 0.1434(4) 0.8187(3) 0.0608(11) Uani 1 1 d . . . C11 C -0.0433(5) 0.2697(3) 1.0518(3) 0.0401(8) Uani 1 1 d . . . H3A H 0.1058 0.3793 0.7492 0.080 Uiso 1 1 d . . . H3B H 0.0679 0.5023 0.7799 0.080 Uiso 1 1 d . . . H4A H 0.3990 0.4576 0.8166 0.080 Uiso 1 1 d . . . H4B H 0.3362 0.4990 0.9237 0.080 Uiso 1 1 d . . . H5A H 0.5131 0.3212 0.9412 0.080 Uiso 1 1 d . . . H5B H 0.3812 0.2593 0.8493 0.080 Uiso 1 1 d . . . H6A H 0.3191 0.3180 1.0668 0.080 Uiso 1 1 d . . . H7A H 0.4350 0.1221 1.0392 0.080 Uiso 1 1 d . . . H7B H 0.2852 0.1149 1.0940 0.080 Uiso 1 1 d . . . H8A H 0.2728 0.0581 0.8734 0.080 Uiso 1 1 d . . . H8B H 0.1648 0.0015 0.9427 0.080 Uiso 1 1 d . . . H10A H -0.1726 0.0809 0.7744 0.080 Uiso 1 1 d . . . H10B H -0.2563 0.2060 0.8031 0.080 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0406(14) 0.0583(18) 0.081(2) 0.0215(14) 0.0176(13) 0.0144(13) N1 0.073(2) 0.065(2) 0.058(2) 0.0061(18) 0.0299(18) 0.0000(18) C1 0.0307(16) 0.0343(17) 0.0324(15) -0.0044(13) 0.0046(12) -0.0006(13) C2 0.0306(17) 0.0363(19) 0.0410(18) -0.0007(15) 0.0011(13) -0.0037(14) C3 0.047(2) 0.058(2) 0.047(2) 0.0133(18) 0.0125(16) -0.0008(18) C4 0.042(2) 0.064(3) 0.064(3) 0.006(2) 0.0188(18) -0.0094(19) C5 0.0276(17) 0.074(3) 0.058(2) -0.004(2) 0.0086(15) -0.0008(18) C6 0.0345(18) 0.048(2) 0.0399(18) -0.0054(16) -0.0006(14) 0.0049(15) C7 0.055(2) 0.058(3) 0.065(3) 0.007(2) -0.0035(19) 0.021(2) C8 0.067(3) 0.039(2) 0.093(3) -0.008(2) 0.010(2) 0.015(2) C9 0.045(2) 0.041(2) 0.0428(19) -0.0081(16) 0.0093(15) -0.0045(16) C10 0.064(3) 0.062(3) 0.055(2) -0.017(2) 0.004(2) -0.013(2) C11 0.043(2) 0.0321(17) 0.0450(19) 0.0018(15) 0.0067(16) 0.0013(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 O1 C2 1.202(4) . ? N1 C11 1.138(4) . ? C1 C11 1.482(4) . ? C1 C2 1.538(5) . ? C1 C9 1.540(5) . ? C1 C6 1.560(4) . ? C2 C3 1.494(5) . ? C3 C4 1.521(5) . ? C4 C5 1.508(6) . ? C5 C6 1.525(5) . ? C6 C7 1.527(6) . ? C7 C8 1.515(6) . ? C8 C9 1.504(5) . ? C9 C10 1.311(5) . ? 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 C1 C2 109.2(3) . . ? C11 C1 C9 108.0(3) . . ? C2 C1 C9 111.6(2) . . ? C11 C1 C6 109.3(2) . . ? C2 C1 C6 115.3(3) . . ? C9 C1 C6 103.1(2) . . ? O1 C2 C3 123.4(3) . . ? O1 C2 C1 120.8(3) . . ? C3 C2 C1 115.8(3) . . ? C2 C3 C4 111.2(3) . . ? C5 C4 C3 110.1(3) . . ? C4 C5 C6 112.9(3) . . ? C5 C6 C7 112.1(3) . . ? C5 C6 C1 111.6(3) . . ? C7 C6 C1 101.9(3) . . ? C8 C7 C6 104.2(3) . . ? C9 C8 C7 106.0(3) . . ? C10 C9 C8 128.5(4) . . ? C10 C9 C1 123.7(3) . . ? C8 C9 C1 107.8(3) . . ? N1 C11 C1 177.3(4) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.280 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.057