# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/277 data_J_Scott_Kerr5 #------------------------------------------------------------------------------ _publ_requested_journal 'J Chem Soc Perkin Trans I' _publ_contact_letter ; Dear Sir, This CIF comprises the supplementary x-ray information needed for the paper "Stereochemical and Mechanistic Features of asymmetric Pauson-Khand processes" by Kennedy, Kerr, Lindsay, Scott and Watson, which has been sent to you by normal post. Please contact me if there are any problems with the cif or its transmission. Yours Sincerely, Alan Kennedy ; _publ_contact_author ; Alan Kennedy Dept. of P & A Chemistry University of Strathclyde 295 Cathedral Street Glasgow G1 1XL Scotland ; _publ_contact_author_phone '0141 548 2016' _publ_contact_author_fax '0141 552 5664' _publ_contact_author_email 'a.r.kennedy@ccsun.strath.ac.uk' #------------------------------------------------------------------------------ _audit_creation_date 'Wed May 21 03:32:24 2000' _audit_creation_method 'from TEXRAY.INF file' _audit_update_record '28/7/2000' #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan' _computing_structure_solution 'SIR' _computing_structure_refinement 'teXsan' _computing_publication_material 'teXsan' #------------------------------------------------------------------------------ _cell_length_a 9.538(2) _cell_length_b 16.348(4) _cell_length_c 8.395(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1308.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123 _cell_measurement_reflns_used 19 _cell_measurement_theta_min 8.5 _cell_measurement_theta_max 11.1 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _exptl_crystal_description 'cut' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.550 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.300 _exptl_crystal_density_diffrn 1.291 _exptl_crystal_density_meas none _chemical_formula_weight 254.33 _chemical_formula_analytical ? _chemical_formula_sum 'C17 H18 O2 ' _chemical_formula_moiety 'C17 H18 O2 ' _chemical_formula_structural ? _chemical_compound_source 'ether/ pet. ether solution' _exptl_crystal_F_000 544.00 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ _diffrn_special_details none _diffrn_ambient_temperature 123 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Rigaku AFC7S' _diffrn_measurement_method '\w/2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% none loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 8 0 -2 7 -2 -3 2 -3 _diffrn_reflns_number 3925 _reflns_number_total 3008 _reflns_number_observed 2550 _reflns_observed_criterion 'I>2\s(I)' _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_reduction_process ? _diffrn_orient_matrix_UB_11 -0.03371 _diffrn_orient_matrix_UB_12 0.05323 _diffrn_orient_matrix_UB_13 -0.04446 _diffrn_orient_matrix_UB_21 0.05667 _diffrn_orient_matrix_UB_22 0.03011 _diffrn_orient_matrix_UB_23 0.08130 _diffrn_orient_matrix_UB_31 0.08152 _diffrn_orient_matrix_UB_32 0.00111 _diffrn_orient_matrix_UB_33 -0.07485 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 68 0.003 0.002 'International Tables' H 0 72 0.000 0.000 'International Tables' O 0 8 0.011 0.006 'International Tables' #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom O(1) -0.0927(1) 0.00781(8) 0.8895(2) 0.0296 Uani ? ? O(2) -0.2158(1) 0.11694(8) 0.4391(2) 0.0287 Uani ? ? C(1) -0.1740(2) 0.05157(10) 0.7746(2) 0.0209 Uani ? ? C(2) -0.2849(2) 0.10494(9) 0.8542(2) 0.0190 Uani ? ? C(3) -0.2624(2) 0.1357(1) 1.0072(2) 0.0243 Uani ? ? C(4) -0.3640(2) 0.1822(1) 1.0823(2) 0.0290 Uani ? ? C(5) -0.4896(2) 0.1994(1) 1.0064(2) 0.0272 Uani ? ? C(6) -0.5133(2) 0.1692(1) 0.8545(2) 0.0242 Uani ? ? C(7) -0.4116(2) 0.1219(1) 0.7796(2) 0.0225 Uani ? ? C(8) -0.0727(2) 0.09921(10) 0.6734(2) 0.0197 Uani ? ? C(9) 0.0597(2) 0.1198(1) 0.7083(2) 0.0218 Uani ? ? C(10) -0.1035(2) 0.12408(10) 0.5082(2) 0.0205 Uani ? ? C(11) 0.0293(2) 0.1584(1) 0.4347(2) 0.0210 Uani ? ? C(12) 0.0918(2) 0.1004(1) 0.3076(2) 0.0244 Uani ? ? C(13) 0.2174(2) 0.1444(1) 0.2321(2) 0.0296 Uani ? ? C(14) 0.3290(2) 0.1447(1) 0.3669(2) 0.0269 Uani ? ? C(15) 0.2543(2) 0.0988(1) 0.5033(2) 0.0226 Uani ? ? C(16) 0.1390(2) 0.1563(1) 0.5709(2) 0.0218 Uani ? ? C(17) 0.1669(2) 0.0362(1) 0.4110(2) 0.0234 Uani ? ? H(1) -0.144(3) -0.031(2) 0.925(3) 0.057(8) Uiso ? ? H(2) -0.227(2) 0.010(1) 0.703(2) 0.016(4) Uiso ? ? H(3) -0.178(2) 0.123(1) 1.056(2) 0.029(5) Uiso ? ? H(4) -0.350(2) 0.202(1) 1.190(3) 0.033(5) Uiso ? ? H(5) -0.559(2) 0.229(1) 1.059(2) 0.021(5) Uiso ? ? H(6) -0.597(2) 0.181(1) 0.799(2) 0.029(5) Uiso ? ? H(7) -0.430(2) 0.100(1) 0.676(3) 0.027(5) Uiso ? ? H(8) 0.103(2) 0.109(1) 0.808(2) 0.021(5) Uiso ? ? H(9) 0.182(2) 0.212(1) 0.596(2) 0.027(5) Uiso ? ? H(10) 0.009(2) 0.211(1) 0.384(2) 0.023(5) Uiso ? ? H(11) 0.023(2) 0.077(1) 0.232(3) 0.033(6) Uiso ? ? H(12) 0.252(2) 0.114(1) 0.144(2) 0.027(5) Uiso ? ? H(13) 0.188(3) 0.199(1) 0.193(3) 0.047(6) Uiso ? ? H(14) 0.415(2) 0.114(1) 0.337(2) 0.022(5) Uiso ? ? H(15) 0.356(3) 0.199(2) 0.403(3) 0.046(7) Uiso ? ? H(16) 0.321(2) 0.075(1) 0.589(2) 0.023(5) Uiso ? ? H(17) 0.225(2) 0.001(1) 0.344(2) 0.021(5) Uiso ? ? H(18) 0.104(2) 0.003(1) 0.473(3) 0.033(6) Uiso ? ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O(1) 0.0254(7) 0.0278(7) 0.0355(7) 0.0050(5) 0.0012(6) 0.0121(6) O(2) 0.0236(6) 0.0342(7) 0.0283(6) 0.0008(6) -0.0044(6) 0.0023(5) C(1) 0.0202(8) 0.0194(7) 0.0230(8) 0.0006(7) 0.0009(7) 0.0022(7) C(2) 0.0184(7) 0.0180(7) 0.0207(8) -0.0038(7) 0.0021(7) 0.0030(6) C(3) 0.0251(8) 0.0245(8) 0.0233(8) -0.0008(7) -0.0041(8) 0.0021(7) C(4) 0.038(1) 0.0271(9) 0.0215(8) -0.0016(8) 0.0026(8) -0.0017(7) C(5) 0.0277(8) 0.0228(8) 0.0312(9) 0.0008(7) 0.0119(8) 0.0019(7) C(6) 0.0172(8) 0.0248(8) 0.0307(9) -0.0006(7) 0.0003(7) 0.0049(7) C(7) 0.0230(8) 0.0247(8) 0.0198(8) -0.0013(7) -0.0006(7) 0.0003(7) C(8) 0.0220(8) 0.0166(7) 0.0203(8) 0.0036(6) 0.0024(7) -0.0018(6) C(9) 0.0238(8) 0.0226(8) 0.0188(8) 0.0019(7) 0.0000(7) -0.0021(7) C(10) 0.0215(7) 0.0174(7) 0.0225(7) 0.0038(6) 0.0007(7) -0.0021(6) C(11) 0.0219(8) 0.0188(8) 0.0222(8) 0.0044(7) 0.0033(7) 0.0032(7) C(12) 0.0245(8) 0.0297(8) 0.0192(8) 0.0037(7) 0.0001(7) -0.0030(7) C(13) 0.0297(9) 0.0343(10) 0.0248(9) 0.0093(8) 0.0069(8) 0.0050(8) C(14) 0.0235(9) 0.0285(9) 0.0287(9) -0.0009(7) 0.0072(8) 0.0007(8) C(15) 0.0206(8) 0.0239(8) 0.0232(8) 0.0024(6) 0.0013(7) 0.0014(7) C(16) 0.0222(8) 0.0200(8) 0.0232(8) -0.0036(7) 0.0019(7) -0.0042(7) C(17) 0.0268(9) 0.0184(7) 0.0250(8) 0.0028(7) 0.0008(7) -0.0035(7) #------------------------------------------------------------------------------ _refine_special_details ; All reflections and their Friedel mates were measured. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '1/\s^2^(F)' _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method Zachariasen_type_2_Gaussian_isotropic _refine_ls_extinction_coef '9.3(27) x 10^-7^' _refine_ls_abs_structure_details ; Analysis of anomalous diffraction was inconclusive. Absolute configuration was based on the known geometry at C(1). ; _refine_ls_number_reflns 2550 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_obs 0.0363 _refine_ls_R_factor_all 0.0518 _refine_ls_wR_factor_obs 0.0429 _refine_ls_wR_factor_all 0.0448 _refine_ls_goodness_of_fit_obs 1.525 _refine_ls_shift/esd_max 0.0050 _refine_diff_density_min -0.22 _refine_diff_density_max 0.23 #------------------------------------------------------------------------------ _geom_special_details ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O(1) C(1) 1.429(2) ? ? yes O(1) H(1) 0.85(3) ? ? no O(2) C(10) 1.223(2) ? ? yes C(1) C(2) 1.526(2) ? ? yes C(1) C(8) 1.504(2) ? ? yes C(1) H(2) 1.04(2) ? ? no C(2) C(3) 1.396(2) ? ? yes C(2) C(7) 1.389(2) ? ? yes C(3) C(4) 1.384(3) ? ? yes C(3) H(3) 0.93(2) ? ? no C(4) C(5) 1.385(3) ? ? yes C(4) H(4) 0.97(2) ? ? no C(5) C(6) 1.386(3) ? ? yes C(5) H(5) 0.93(2) ? ? no C(6) C(7) 1.390(2) ? ? yes C(6) H(6) 0.94(2) ? ? no C(7) H(7) 0.96(2) ? ? no C(8) C(9) 1.339(2) ? ? yes C(8) C(10) 1.475(2) ? ? yes C(9) C(16) 1.503(2) ? ? yes C(9) H(8) 0.95(2) ? ? no C(10) C(11) 1.516(2) ? ? yes C(11) C(12) 1.548(2) ? ? yes C(11) C(16) 1.550(2) ? ? yes C(11) H(10) 0.98(2) ? ? no C(12) C(13) 1.534(3) ? ? yes C(12) C(17) 1.539(3) ? ? yes C(12) H(11) 0.99(2) ? ? no C(13) C(14) 1.554(3) ? ? yes C(13) H(12) 0.95(2) ? ? no C(13) H(13) 1.00(2) ? ? no C(14) C(15) 1.544(2) ? ? yes C(14) H(14) 0.99(2) ? ? no C(14) H(15) 0.97(2) ? ? no C(15) C(16) 1.554(2) ? ? yes C(15) C(17) 1.530(3) ? ? yes C(15) H(16) 1.03(2) ? ? no C(16) H(9) 1.01(2) ? ? no C(17) H(17) 0.98(2) ? ? no C(17) H(18) 0.97(2) ? ? no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O(1) C(1) C(2) 111.5(1) ? ? ? yes O(1) C(1) C(8) 107.0(1) ? ? ? yes C(2) C(1) C(8) 113.4(1) ? ? ? yes C(1) C(2) C(3) 120.2(1) ? ? ? yes C(1) C(2) C(7) 121.3(1) ? ? ? yes C(3) C(2) C(7) 118.5(2) ? ? ? yes C(2) C(3) C(4) 120.6(2) ? ? ? yes C(3) C(4) C(5) 120.5(2) ? ? ? yes C(4) C(5) C(6) 119.5(2) ? ? ? yes C(5) C(6) C(7) 120.0(2) ? ? ? yes C(2) C(7) C(6) 120.9(2) ? ? ? yes C(1) C(8) C(9) 127.8(2) ? ? ? yes C(1) C(8) C(10) 123.1(1) ? ? ? yes C(9) C(8) C(10) 108.9(1) ? ? ? yes C(8) C(9) C(16) 114.0(1) ? ? ? yes O(2) C(10) C(8) 126.4(2) ? ? ? yes O(2) C(10) C(11) 125.0(2) ? ? ? yes C(8) C(10) C(11) 108.5(1) ? ? ? yes C(10) C(11) C(12) 112.1(1) ? ? ? yes C(10) C(11) C(16) 104.8(1) ? ? ? yes C(12) C(11) C(16) 103.6(1) ? ? ? yes C(11) C(12) C(13) 107.4(1) ? ? ? yes C(11) C(12) C(17) 102.0(1) ? ? ? yes C(13) C(12) C(17) 100.9(1) ? ? ? yes C(12) C(13) C(14) 103.6(1) ? ? ? yes C(13) C(14) C(15) 102.8(1) ? ? ? yes C(14) C(15) C(16) 107.7(1) ? ? ? yes C(14) C(15) C(17) 101.6(1) ? ? ? yes C(16) C(15) C(17) 101.8(1) ? ? ? yes C(9) C(16) C(11) 103.6(1) ? ? ? yes C(9) C(16) C(15) 113.3(1) ? ? ? yes C(11) C(16) C(15) 102.8(1) ? ? ? yes C(12) C(17) C(15) 94.8(1) ? ? ? yes #===END