# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Gerald Pattenden' _publ_contact_author_address ; School of Chemistry The University of Nottingham University Park Nottingham NG7 2RD UNITED KINGDOM ; _publ_contact_author_email GP@NOTTINGHAM.AC.UK _publ_section_title ; Unsaturated and Cyclopropyl Acyl Radicals, and their Ketene Alkyl Radical Equivalents. Ring Synthesis and Tandem Cyclisation Reactions. ; loop_ _publ_author_name 'Gerald Pattenden' 'Nicole M. Harrington-Frost' 'Christopher J. Hayes' 'Nicola M.A. Herbert' data_NOCOOH _database_code_depnum_ccdc_archive 'CCDC 253408' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C9 H14 O2' _chemical_formula_sum 'C9 H14 O2' _chemical_formula_weight 154.20 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 7.320(8) _cell_length_b 8.396(6) _cell_length_c 13.236(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.07(9) _cell_angle_gamma 90.00 _cell_volume 813.5(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(2) _cell_measurement_reflns_used 15 _cell_measurement_theta_min 11 _cell_measurement_theta_max 13 _exptl_crystal_description column _exptl_crystal_colour colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 336 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(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 'Stoe Stadi-4 four-circle' _diffrn_measurement_method omega/theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 'random variation +/-5.3' _diffrn_reflns_number 2372 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0474 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1426 _reflns_number_gt 1096 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (Stoe & Cie, 1997a)' _computing_cell_refinement 'STADI4 (Stoe & Cie, 1997a)' _computing_data_reduction 'X-RED (Stoe & Cie, 1997b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1994)' _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 w=1/[\s^2^(Fo^2^)+(0.038P)^2^+0.650P] 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 0.015(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1426 _refine_ls_number_parameters 102 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0651 _refine_ls_R_factor_gt 0.0485 _refine_ls_wR_factor_ref 0.127 _refine_ls_wR_factor_gt 0.112 _refine_ls_goodness_of_fit_ref 1.05 _refine_ls_restrained_S_all 1.05 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1218(3) 0.2667(3) 1.00061(16) 0.0276(5) Uani 1 d . . . O1 O -0.0843(2) 0.2241(2) 1.08668(11) 0.0346(5) Uani 1 d . . . C2 C 0.0147(3) 0.3298(3) 0.93074(15) 0.0263(5) Uani 1 d . . . H2 H -0.0288 0.4127 0.8821 0.032 Uiso 1 calc R . . C3 C 0.1298(3) 0.1951(3) 0.88634(16) 0.0268(5) Uani 1 d . . . H3 H 0.1162 0.0909 0.9221 0.032 Uiso 1 calc R . . C4 C 0.1358(3) 0.1819(3) 0.77305(16) 0.0275(5) Uani 1 d . . . H4 H 0.2470 0.1204 0.7529 0.033 Uiso 1 calc R . . O4 O 0.1450(2) 0.33744(18) 0.73050(12) 0.0336(4) Uani 1 d . . . H4O H 0.2228 0.3386 0.6839 0.050 Uiso 1 calc R . . C5 C -0.0348(3) 0.0948(3) 0.73471(16) 0.0323(6) Uani 1 d . . . H5A H -0.0291 -0.0166 0.7589 0.039 Uiso 1 calc R . . H5B H -0.0294 0.0918 0.6600 0.039 Uiso 1 calc R . . C6 C -0.2211(3) 0.1643(3) 0.76540(17) 0.0341(6) Uani 1 d . . . H6A H -0.3110 0.1355 0.7126 0.041 Uiso 1 calc R . . H6B H -0.2106 0.2819 0.7656 0.041 Uiso 1 calc R . . C7 C -0.2988(3) 0.1122(3) 0.86845(18) 0.0387(6) Uani 1 d . . . H7A H -0.2253 0.0210 0.8928 0.046 Uiso 1 calc R . . H7B H -0.4246 0.0727 0.8572 0.046 Uiso 1 calc R . . C8 C -0.3059(3) 0.2378(3) 0.95429(17) 0.0353(6) Uani 1 d . . . H8A H -0.3537 0.3393 0.9268 0.042 Uiso 1 calc R . . H8B H -0.3912 0.2008 1.0073 0.042 Uiso 1 calc R . . C9 C 0.2165(3) 0.3227(3) 0.94840(17) 0.0327(6) Uani 1 d . . . H9A H 0.2938 0.4017 0.9130 0.039 Uiso 1 calc R . . H9B H 0.2592 0.2939 1.0170 0.039 Uiso 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 0.0317(12) 0.0260(12) 0.0250(11) -0.0026(9) 0.0029(9) 0.0041(10) O1 0.0374(9) 0.0434(10) 0.0229(8) 0.0018(7) 0.0035(7) 0.0011(8) C2 0.0283(11) 0.0276(12) 0.0231(10) -0.0025(9) 0.0021(8) 0.0017(9) C3 0.0275(11) 0.0280(12) 0.0249(11) 0.0012(9) 0.0008(9) 0.0002(9) C4 0.0320(11) 0.0247(11) 0.0258(11) -0.0014(9) 0.0041(9) 0.0003(10) O4 0.0434(10) 0.0280(9) 0.0296(9) 0.0036(7) 0.0117(7) 0.0011(8) C5 0.0425(13) 0.0296(13) 0.0248(11) -0.0028(9) -0.0016(10) 0.0005(11) C6 0.0319(12) 0.0429(14) 0.0275(12) -0.0015(10) -0.0077(9) -0.0003(11) C7 0.0304(12) 0.0505(15) 0.0351(13) -0.0010(11) -0.0027(10) -0.0065(12) C8 0.0266(12) 0.0478(15) 0.0316(12) 0.0037(11) 0.0041(9) 0.0023(11) C9 0.0289(12) 0.0404(14) 0.0288(11) -0.0019(10) 0.0031(9) -0.0038(11) _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 O1 1.225(3) . ? C1 C2 1.462(3) . ? C1 C8 1.500(3) . ? C2 C9 1.497(3) . ? C2 C3 1.529(3) . ? C3 C9 1.492(3) . ? C3 C4 1.504(3) . ? C4 O4 1.424(3) . ? C4 C5 1.533(3) . ? C5 C6 1.538(4) . ? C6 C7 1.542(4) . ? C7 C8 1.551(4) . ? 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 O1 C1 C2 122.8(2) . . ? O1 C1 C8 122.2(2) . . ? C2 C1 C8 114.5(2) . . ? C1 C2 C9 124.2(2) . . ? C1 C2 C3 110.63(19) . . ? C9 C2 C3 59.07(15) . . ? C9 C3 C4 126.1(2) . . ? C9 C3 C2 59.40(16) . . ? C4 C3 C2 117.04(18) . . ? O4 C4 C3 109.15(18) . . ? O4 C4 C5 110.19(18) . . ? C3 C4 C5 109.9(2) . . ? C4 C5 C6 117.0(2) . . ? C5 C6 C7 117.0(2) . . ? C6 C7 C8 117.9(2) . . ? C1 C8 C7 112.3(2) . . ? C3 C9 C2 61.53(15) . . ? 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 O1 C1 C2 C9 11.4(3) . . . . ? C8 C1 C2 C9 -160.8(2) . . . . ? O1 C1 C2 C3 77.3(3) . . . . ? C8 C1 C2 C3 -94.9(2) . . . . ? C1 C2 C3 C9 -118.3(2) . . . . ? C1 C2 C3 C4 123.9(2) . . . . ? C9 C2 C3 C4 -117.8(2) . . . . ? C9 C3 C4 O4 -31.0(3) . . . . ? C2 C3 C4 O4 39.5(3) . . . . ? C9 C3 C4 C5 -151.9(2) . . . . ? C2 C3 C4 C5 -81.5(2) . . . . ? O4 C4 C5 C6 -64.7(3) . . . . ? C3 C4 C5 C6 55.7(3) . . . . ? C4 C5 C6 C7 -85.5(3) . . . . ? C5 C6 C7 C8 110.0(3) . . . . ? O1 C1 C8 C7 -110.4(3) . . . . ? C2 C1 C8 C7 61.8(3) . . . . ? C6 C7 C8 C1 -76.3(3) . . . . ? C4 C3 C9 C2 102.9(2) . . . . ? C1 C2 C9 C3 95.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.929 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.929 _refine_diff_density_max 0.18 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.05 #=== END of CIF