# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/426 data_global # 1. SUBMISSION DETAILS _publ_contact_autor ; Prof. Dr. G\"unter Haufe Organisch-Chemisches Institut der Universit\"at M\"unster Corrensstrasse 40 D-48149 M\"unster Bundesrepublik Deutschland ; _publ_contact_author_phone '49 251 83-33281' _publ_contact_author_fax '49 251 83-39772' _publ_contact-Author_email 'haufe@uni-muenster.de' _publ_requested_journal 'Perkin Trans. I' _publ_requested_coeditor_name ? _publ_contact_letter ; Publication is sent to "Perkin Trans. I" (Ref. B001618G) ; #========================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Reactions of Ployfluorinated Cyclohexadienes with Diazoalkanes I. Formation of Cyclopropanes from Ployfluorinated 2,4-Cyclohexdienones with Diazomethane and Phenyl Diazomethane. ; loop_ _publ_author_name _publ_author_address 'Kovtonyuk, V.N.' ; N.N.Vorozhtsov Institute of Organic Chemistry 630090 Novosibirsk Russian Federation ; 'Kobrina, L.S.' ; N.N.Vorozhtsov Institute of Organic Chemistry 630090 Novosibirsk Russian Federation ; 'Gatilov, Yu.V.' ; N.N.Vorozhtsov Institute of Organic Chemistry 630090 Novosibirsk Russian Federation ; 'Bagryanskaya, I.Yu.' ; N.N.Vorozhtsov Institute of Organic Chemistry 630090 Novosibirsk Russian Federation ; 'Fr\"ohlich, Roland' ; Organisch-Chemisches Institut der Universit\"at M\"unster Corrensstrasse 40 D-48149 M\"unster Bundesrepublik Deutschland ; 'Haufe, G\"unter' ; Organisch-Chemisches Institut der Universit\"at M\"unster Corrensstrasse 40 D-48149 M\"unster Bundesrepublik Deutschland ; #========================================================================== data_Kovtonyuk_izomer_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 7-endo-phenyl-1,2,3,4,6-pentafluoro-4-chloro- -bicyclo[4.1.0]hept-2-ene-5-one ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 Cl F5 O' _chemical_formula_weight 308.63 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.914(6) _cell_length_b 10.407(7) _cell_length_c 13.607(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.68(5) _cell_angle_gamma 90.00 _cell_volume 1256.1(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9 _cell_measurement_theta_min 23.9 _cell_measurement_theta_max 26.4 _exptl_crystal_description 'unregular prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 3.250 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.488 _exptl_absorpt_correction_T_max 0.958 _exptl_special_details ; The crystal was placed into polyethylenic capillar to avoid evapouration. Nevertheless standards dropped by 23.65%. Appropriate correction was applied. ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Syntex P21' _diffrn_measurement_method theta/2theta _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 23.65 _diffrn_reflns_number 2312 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0609 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 2 _diffrn_reflns_theta_min 4.99 _diffrn_reflns_theta_max 70.05 _reflns_number_total 2056 _reflns_number_gt 1152 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Syntex P21' _computing_cell_refinement 'Syntex P21' _computing_data_reduction 'XTAPE' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP' _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^)+(0.0756P)^2^+0.3502P] 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 refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0036(7) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2056 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1177 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1733 _refine_ls_wR_factor_gt 0.1399 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.8958(6) -0.1759(4) 0.5253(4) 0.0635(15) Uani 1 d . . . F1 F 0.9813(4) -0.1223(3) 0.6040(3) 0.1063(14) Uani 1 d . . . C2 C 0.7339(7) -0.1463(5) 0.5238(4) 0.0651(14) Uani 1 d . . . F2 F 0.6786(5) -0.1536(3) 0.6103(3) 0.1056(12) Uani 1 d . . . C3 C 0.6474(5) -0.1283(4) 0.4419(4) 0.0594(13) Uani 1 d . . . F3 F 0.4965(3) -0.1197(3) 0.4438(3) 0.0951(11) Uani 1 d . . . C4 C 0.6993(6) -0.1191(4) 0.3436(4) 0.0629(14) Uani 1 d . . . F4 F 0.6192(3) -0.2034(3) 0.2815(2) 0.0926(12) Uani 1 d . . . Cl4 Cl 0.6622(2) 0.03714(15) 0.29513(12) 0.0996(7) Uani 1 d . . . C5 C 0.8688(6) -0.1485(5) 0.3368(4) 0.0625(13) Uani 1 d . . . O5 O 0.9180(5) -0.1426(4) 0.2593(3) 0.0968(14) Uani 1 d . . . C6 C 0.9612(5) -0.1804(5) 0.4302(4) 0.0651(15) Uani 1 d . . . F6 F 1.1063(3) -0.1376(3) 0.4288(3) 0.1045(13) Uani 1 d . . . C7 C 0.9466(5) -0.3027(5) 0.4881(4) 0.0658(16) Uani 1 d . . . H7 H 1.032(6) -0.320(6) 0.526(4) 0.094(18) Uiso 1 d . . . C8 C 0.8407(5) -0.4103(4) 0.4564(4) 0.0520(13) Uani 1 d . . . C9 C 0.7587(6) -0.4668(5) 0.5247(5) 0.0631(14) Uani 1 d . . . H9 H 0.760(6) -0.440(6) 0.590(4) 0.088(19) Uiso 1 d . . . C10 C 0.6672(6) -0.5709(6) 0.4970(6) 0.0758(17) Uani 1 d . . . H10 H 0.631(7) -0.614(5) 0.547(4) 0.08(2) Uiso 1 d . . . C11 C 0.6584(6) -0.6171(6) 0.4037(6) 0.0779(19) Uani 1 d . . . H11 H 0.609(6) -0.687(6) 0.383(4) 0.089(18) Uiso 1 d . . . C12 C 0.7387(7) -0.5616(5) 0.3360(5) 0.0757(18) Uani 1 d . . . H12 H 0.738(7) -0.600(6) 0.273(5) 0.11(2) Uiso 1 d . . . C13 C 0.8320(6) -0.4592(5) 0.3630(4) 0.0634(14) Uani 1 d . . . H13 H 0.877(5) -0.414(4) 0.324(3) 0.040(14) Uiso 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 C1 0.070(3) 0.040(3) 0.075(3) -0.005(2) -0.018(3) 0.005(2) F1 0.141(3) 0.0555(19) 0.108(2) -0.0119(17) -0.058(2) -0.0015(18) C2 0.092(4) 0.042(3) 0.064(3) -0.006(2) 0.021(3) 0.005(3) F2 0.149(3) 0.090(3) 0.082(2) 0.005(2) 0.035(2) 0.030(2) C3 0.054(3) 0.046(3) 0.079(4) -0.002(2) 0.009(3) 0.012(2) F3 0.0571(19) 0.089(2) 0.141(3) -0.001(2) 0.0206(18) 0.0147(17) C4 0.063(3) 0.049(3) 0.074(3) -0.006(3) -0.009(3) 0.011(2) F4 0.077(2) 0.091(2) 0.104(2) -0.038(2) -0.0226(17) 0.0098(17) Cl4 0.1228(14) 0.0718(10) 0.1025(12) 0.0193(8) 0.0032(9) 0.0394(9) C5 0.060(3) 0.047(3) 0.083(4) 0.001(3) 0.017(3) 0.001(2) O5 0.092(3) 0.099(3) 0.105(3) 0.018(3) 0.036(3) 0.010(2) C6 0.043(3) 0.047(3) 0.104(4) 0.009(3) -0.001(3) -0.002(2) F6 0.0507(17) 0.066(2) 0.192(4) 0.021(2) -0.009(2) -0.0120(14) C7 0.057(3) 0.042(3) 0.092(4) 0.004(3) -0.023(3) 0.000(2) C8 0.049(3) 0.030(2) 0.075(3) -0.003(2) -0.007(2) 0.0087(19) C9 0.060(3) 0.049(3) 0.080(4) -0.006(3) 0.009(3) 0.001(3) C10 0.054(3) 0.057(4) 0.118(5) -0.005(4) 0.018(3) -0.006(3) C11 0.054(3) 0.052(3) 0.123(6) -0.019(4) -0.013(3) -0.001(3) C12 0.084(4) 0.055(3) 0.083(4) -0.014(3) -0.016(3) 0.009(3) C13 0.068(3) 0.047(3) 0.074(4) 0.001(3) 0.005(3) 0.003(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 C1 F1 1.369(5) . ? C1 C6 1.471(8) . ? C1 C2 1.474(7) . ? C1 C7 1.499(7) . ? C2 C3 1.304(7) . ? C2 F2 1.323(6) . ? C3 F3 1.351(5) . ? C3 C4 1.461(7) . ? C4 F4 1.369(5) . ? C4 C5 1.553(7) . ? C4 Cl4 1.774(5) . ? C5 O5 1.184(6) . ? C5 C6 1.482(7) . ? C6 F6 1.371(5) . ? C6 C7 1.509(7) . ? C7 C8 1.500(6) . ? C8 C13 1.365(7) . ? C8 C9 1.370(7) . ? C9 C10 1.386(7) . ? C10 C11 1.353(9) . ? C11 C12 1.351(9) . ? C12 C13 1.380(8) . ? 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 F1 C1 C6 117.6(5) . . ? F1 C1 C2 113.2(5) . . ? C6 C1 C2 117.8(4) . . ? F1 C1 C7 117.3(4) . . ? C6 C1 C7 61.1(4) . . ? C2 C1 C7 120.5(4) . . ? C3 C2 F2 121.9(6) . . ? C3 C2 C1 122.5(5) . . ? F2 C2 C1 115.2(5) . . ? C2 C3 F3 119.9(5) . . ? C2 C3 C4 125.3(5) . . ? F3 C3 C4 114.8(4) . . ? F4 C4 C3 109.3(5) . . ? F4 C4 C5 106.7(4) . . ? C3 C4 C5 116.1(4) . . ? F4 C4 Cl4 106.9(3) . . ? C3 C4 Cl4 109.7(4) . . ? C5 C4 Cl4 107.7(4) . . ? O5 C5 C6 123.5(5) . . ? O5 C5 C4 119.5(5) . . ? C6 C5 C4 117.0(5) . . ? F6 C6 C1 117.3(5) . . ? F6 C6 C5 111.1(5) . . ? C1 C6 C5 120.8(4) . . ? F6 C6 C7 114.3(4) . . ? C1 C6 C7 60.4(4) . . ? C5 C6 C7 124.6(4) . . ? C1 C7 C8 123.5(4) . . ? C1 C7 C6 58.6(3) . . ? C8 C7 C6 124.3(4) . . ? C13 C8 C9 119.1(5) . . ? C13 C8 C7 121.5(5) . . ? C9 C8 C7 119.2(5) . . ? C8 C9 C10 119.4(6) . . ? C11 C10 C9 120.7(7) . . ? C12 C11 C10 120.2(6) . . ? C11 C12 C13 119.6(6) . . ? C8 C13 C12 120.9(6) . . ? 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 F1 C1 C2 C3 144.9(5) . . . . ? C6 C1 C2 C3 2.2(7) . . . . ? C7 C1 C2 C3 -68.9(7) . . . . ? F1 C1 C2 F2 -42.5(6) . . . . ? C6 C1 C2 F2 174.8(4) . . . . ? C7 C1 C2 F2 103.7(6) . . . . ? F2 C2 C3 F3 -1.5(7) . . . . ? C1 C2 C3 F3 170.6(4) . . . . ? F2 C2 C3 C4 180.0(5) . . . . ? C1 C2 C3 C4 -7.9(8) . . . . ? C2 C3 C4 F4 127.9(5) . . . . ? F3 C3 C4 F4 -50.6(5) . . . . ? C2 C3 C4 C5 7.2(7) . . . . ? F3 C3 C4 C5 -171.4(4) . . . . ? C2 C3 C4 Cl4 -115.2(5) . . . . ? F3 C3 C4 Cl4 66.3(5) . . . . ? F4 C4 C5 O5 58.0(6) . . . . ? C3 C4 C5 O5 -179.9(5) . . . . ? Cl4 C4 C5 O5 -56.5(6) . . . . ? F4 C4 C5 C6 -123.2(5) . . . . ? C3 C4 C5 C6 -1.1(6) . . . . ? Cl4 C4 C5 C6 122.3(4) . . . . ? F1 C1 C6 F6 3.8(6) . . . . ? C2 C1 C6 F6 144.8(4) . . . . ? C7 C1 C6 F6 -103.9(4) . . . . ? F1 C1 C6 C5 -137.4(4) . . . . ? C2 C1 C6 C5 3.6(7) . . . . ? C7 C1 C6 C5 114.9(5) . . . . ? F1 C1 C6 C7 107.6(4) . . . . ? C2 C1 C6 C7 -111.3(5) . . . . ? O5 C5 C6 F6 31.6(7) . . . . ? C4 C5 C6 F6 -147.2(4) . . . . ? O5 C5 C6 C1 174.9(5) . . . . ? C4 C5 C6 C1 -3.8(7) . . . . ? O5 C5 C6 C7 -111.8(7) . . . . ? C4 C5 C6 C7 69.4(7) . . . . ? F1 C1 C7 C8 139.2(5) . . . . ? C6 C1 C7 C8 -112.8(5) . . . . ? C2 C1 C7 C8 -5.7(8) . . . . ? F1 C1 C7 C6 -108.0(6) . . . . ? C2 C1 C7 C6 107.1(5) . . . . ? F6 C6 C7 C1 108.7(5) . . . . ? C5 C6 C7 C1 -108.9(6) . . . . ? F6 C6 C7 C8 -139.8(5) . . . . ? C1 C6 C7 C8 111.5(6) . . . . ? C5 C6 C7 C8 2.6(9) . . . . ? C1 C7 C8 C13 120.7(6) . . . . ? C6 C7 C8 C13 48.5(7) . . . . ? C1 C7 C8 C9 -64.0(6) . . . . ? C6 C7 C8 C9 -136.2(5) . . . . ? C13 C8 C9 C10 -1.0(7) . . . . ? C7 C8 C9 C10 -176.4(4) . . . . ? C8 C9 C10 C11 0.2(8) . . . . ? C9 C10 C11 C12 -0.4(9) . . . . ? C10 C11 C12 C13 1.3(9) . . . . ? C9 C8 C13 C12 2.0(7) . . . . ? C7 C8 C13 C12 177.3(4) . . . . ? C11 C12 C13 C8 -2.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.816 _diffrn_reflns_theta_full 70.05 _diffrn_measured_fraction_theta_full 0.815 _refine_diff_density_max 0.192 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.053 #========================================================================== data_haf_960 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H6 Cl F5 O' _chemical_formula_weight 308.63 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.205(1) _cell_length_b 13.755(1) _cell_length_c 7.725(1) _cell_angle_alpha 90.00 _cell_angle_beta 91.28(1) _cell_angle_gamma 90.00 _cell_volume 1190.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.377 _exptl_absorpt_correction_type 'SORTAV (Blessing, 1995 & 1997)' _exptl_absorpt_correction_T_min 0.8639 _exptl_absorpt_correction_T_max 0.9284 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode Nonius FR591' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9988 _diffrn_reflns_av_R_equivalents 0.0366 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 30.48 _reflns_number_total 3517 _reflns_number_gt 2683 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V., 1998)' _computing_cell_refinement 'Collect (Nonius B.V., 1998)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Siemens Analytical)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0341P)^2^+0.5607P] 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 'refined as riding atoms' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3517 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.0939 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 C2 C 0.60304(13) 0.87993(11) 0.3538(2) 0.0304(3) Uani 1 1 d . . . O2 O 0.50230(10) 0.85245(10) 0.36312(18) 0.0453(3) Uani 1 1 d . . . C3 C 0.68395(15) 0.83537(12) 0.2159(2) 0.0333(3) Uani 1 1 d . . . F3 F 0.64528(10) 0.74237(8) 0.18639(14) 0.0456(3) Uani 1 1 d . . . Cl3 Cl 0.66234(5) 0.89917(4) 0.01828(5) 0.05004(15) Uani 1 1 d . . . C4 C 0.81213(14) 0.83330(12) 0.2665(2) 0.0342(3) Uani 1 1 d . . . F4 F 0.88122(10) 0.78339(9) 0.15869(15) 0.0526(3) Uani 1 1 d . . . C5 C 0.85920(13) 0.88194(12) 0.3970(2) 0.0319(3) Uani 1 1 d . . . F5 F 0.97740(8) 0.88209(9) 0.42558(15) 0.0473(3) Uani 1 1 d . . . C6 C 0.79116(13) 0.94584(12) 0.51129(18) 0.0290(3) Uani 1 1 d . . . F6 F 0.83102(9) 0.94228(8) 0.67927(12) 0.0412(2) Uani 1 1 d . . . C1 C 0.65802(13) 0.94854(12) 0.48079(18) 0.0284(3) Uani 1 1 d . . . F1 F 0.59223(8) 0.95433(7) 0.62601(12) 0.0370(2) Uani 1 1 d . . . C7 C 0.73469(13) 1.03821(11) 0.44784(19) 0.0293(3) Uani 1 1 d . . . H7 H 0.7281 1.0881 0.5413 0.035 Uiso 1 1 calc R . . C8 C 0.75619(13) 1.08241(11) 0.27472(19) 0.0287(3) Uani 1 1 d . . . C13 C 0.66389(14) 1.12926(12) 0.1862(2) 0.0346(3) Uani 1 1 d . . . H13 H 0.5867 1.1318 0.2345 0.042 Uiso 1 1 calc R . . C12 C 0.68376(17) 1.17242(14) 0.0275(2) 0.0430(4) Uani 1 1 d . . . H12 H 0.6203 1.2047 -0.0325 0.052 Uiso 1 1 calc R . . C11 C 0.79520(19) 1.16866(15) -0.0436(3) 0.0487(5) Uani 1 1 d . . . H11 H 0.8082 1.1971 -0.1536 0.058 Uiso 1 1 calc R . . C10 C 0.88796(17) 1.12350(15) 0.0450(3) 0.0504(5) Uani 1 1 d . . . H10 H 0.9652 1.1219 -0.0032 0.061 Uiso 1 1 calc R . . C9 C 0.86891(15) 1.08053(13) 0.2038(2) 0.0385(4) Uani 1 1 d . . . H9 H 0.9331 1.0497 0.2645 0.046 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 C2 0.0323(7) 0.0296(8) 0.0294(7) 0.0063(6) -0.0006(6) -0.0022(6) O2 0.0327(6) 0.0456(8) 0.0574(8) 0.0049(6) -0.0007(5) -0.0083(5) C3 0.0479(9) 0.0265(8) 0.0256(7) -0.0008(6) 0.0025(6) -0.0086(6) F3 0.0630(7) 0.0307(5) 0.0431(6) -0.0046(4) 0.0014(5) -0.0140(5) Cl3 0.0783(3) 0.0474(3) 0.02413(19) 0.00407(17) -0.00568(19) -0.0145(2) C4 0.0412(8) 0.0308(8) 0.0311(8) -0.0021(6) 0.0128(6) 0.0001(6) F4 0.0588(7) 0.0480(7) 0.0523(7) -0.0160(5) 0.0258(5) 0.0002(5) C5 0.0286(7) 0.0354(8) 0.0318(8) 0.0038(6) 0.0044(6) 0.0020(6) F5 0.0294(5) 0.0568(7) 0.0557(7) 0.0012(5) 0.0012(4) 0.0042(4) C6 0.0332(7) 0.0334(8) 0.0203(6) 0.0002(6) -0.0013(5) -0.0004(6) F6 0.0487(6) 0.0513(6) 0.0231(4) 0.0011(4) -0.0063(4) 0.0004(5) C1 0.0303(7) 0.0322(8) 0.0229(6) 0.0029(6) 0.0069(5) 0.0016(6) F1 0.0429(5) 0.0398(5) 0.0289(5) 0.0041(4) 0.0151(4) 0.0045(4) C7 0.0347(7) 0.0273(7) 0.0259(7) -0.0022(6) 0.0024(5) -0.0033(6) C8 0.0337(7) 0.0257(7) 0.0268(7) 0.0003(6) 0.0029(5) -0.0055(6) C13 0.0359(8) 0.0322(8) 0.0359(8) 0.0037(7) 0.0034(6) 0.0002(6) C12 0.0532(10) 0.0362(9) 0.0394(9) 0.0088(7) -0.0007(8) 0.0043(8) C11 0.0672(12) 0.0420(11) 0.0374(9) 0.0140(8) 0.0120(8) -0.0008(9) C10 0.0456(10) 0.0532(12) 0.0533(11) 0.0148(9) 0.0200(8) -0.0032(9) C9 0.0332(8) 0.0407(9) 0.0417(9) 0.0072(7) 0.0039(7) -0.0052(7) _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 C2 O2 1.1941(19) . ? C2 C1 1.485(2) . ? C2 C3 1.541(2) . ? C3 F3 1.3680(18) . ? C3 C4 1.480(2) . ? C3 Cl3 1.7727(16) . ? C4 C5 1.311(2) . ? C4 F4 1.3388(18) . ? C5 F5 1.3378(18) . ? C5 C6 1.471(2) . ? C6 F6 1.3637(17) . ? C6 C7 1.497(2) . ? C6 C1 1.506(2) . ? C1 F1 1.3584(15) . ? C1 C7 1.528(2) . ? C7 C8 1.494(2) . ? C8 C13 1.386(2) . ? C8 C9 1.388(2) . ? C13 C12 1.384(2) . ? C12 C11 1.376(3) . ? C11 C10 1.379(3) . ? C10 C9 1.382(2) . ? 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 O2 C2 C1 122.67(15) . . ? O2 C2 C3 119.17(15) . . ? C1 C2 C3 117.88(13) . . ? F3 C3 C4 109.14(14) . . ? F3 C3 C2 107.34(12) . . ? C4 C3 C2 114.05(13) . . ? F3 C3 Cl3 106.43(10) . . ? C4 C3 Cl3 110.48(11) . . ? C2 C3 Cl3 109.09(11) . . ? C5 C4 F4 120.77(15) . . ? C5 C4 C3 124.37(14) . . ? F4 C4 C3 114.64(14) . . ? C4 C5 F5 120.50(14) . . ? C4 C5 C6 124.17(14) . . ? F5 C5 C6 115.11(14) . . ? F6 C6 C5 112.75(13) . . ? F6 C6 C7 117.98(13) . . ? C5 C6 C7 122.11(13) . . ? F6 C6 C1 116.88(12) . . ? C5 C6 C1 116.47(13) . . ? C7 C6 C1 61.16(10) . . ? F1 C1 C2 110.98(12) . . ? F1 C1 C6 115.23(12) . . ? C2 C1 C6 118.86(13) . . ? F1 C1 C7 114.07(13) . . ? C2 C1 C7 129.01(12) . . ? C6 C1 C7 59.14(10) . . ? C8 C7 C6 124.28(13) . . ? C8 C7 C1 125.48(13) . . ? C6 C7 C1 59.70(10) . . ? C13 C8 C9 119.29(15) . . ? C13 C8 C7 119.85(13) . . ? C9 C8 C7 120.81(15) . . ? C12 C13 C8 120.22(15) . . ? C11 C12 C13 120.16(17) . . ? C12 C11 C10 119.95(17) . . ? C11 C10 C9 120.21(17) . . ? C10 C9 C8 120.14(17) . . ? 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 O2 C2 C3 F3 -29.2(2) . . . . ? C1 C2 C3 F3 144.86(13) . . . . ? O2 C2 C3 C4 -150.24(15) . . . . ? C1 C2 C3 C4 23.8(2) . . . . ? O2 C2 C3 Cl3 85.71(16) . . . . ? C1 C2 C3 Cl3 -100.22(14) . . . . ? F3 C3 C4 C5 -133.90(16) . . . . ? C2 C3 C4 C5 -13.9(2) . . . . ? Cl3 C3 C4 C5 109.41(17) . . . . ? F3 C3 C4 F4 51.52(18) . . . . ? C2 C3 C4 F4 171.54(13) . . . . ? Cl3 C3 C4 F4 -65.16(16) . . . . ? F4 C4 C5 F5 -0.4(2) . . . . ? C3 C4 C5 F5 -174.68(14) . . . . ? F4 C4 C5 C6 174.00(15) . . . . ? C3 C4 C5 C6 -0.3(3) . . . . ? C4 C5 C6 F6 143.57(16) . . . . ? F5 C5 C6 F6 -41.75(19) . . . . ? C4 C5 C6 C7 -66.7(2) . . . . ? F5 C5 C6 C7 107.99(16) . . . . ? C4 C5 C6 C1 4.4(2) . . . . ? F5 C5 C6 C1 179.10(13) . . . . ? O2 C2 C1 F1 15.9(2) . . . . ? C3 C2 C1 F1 -157.96(13) . . . . ? O2 C2 C1 C6 152.99(15) . . . . ? C3 C2 C1 C6 -20.9(2) . . . . ? O2 C2 C1 C7 -134.90(17) . . . . ? C3 C2 C1 C7 51.2(2) . . . . ? F6 C6 C1 F1 4.6(2) . . . . ? C5 C6 C1 F1 142.08(14) . . . . ? C7 C6 C1 F1 -104.11(14) . . . . ? F6 C6 C1 C2 -130.74(14) . . . . ? C5 C6 C1 C2 6.7(2) . . . . ? C7 C6 C1 C2 120.52(15) . . . . ? F6 C6 C1 C7 108.74(15) . . . . ? C5 C6 C1 C7 -113.81(15) . . . . ? F6 C6 C7 C8 138.49(15) . . . . ? C5 C6 C7 C8 -9.8(2) . . . . ? C1 C6 C7 C8 -114.54(16) . . . . ? F6 C6 C7 C1 -106.97(14) . . . . ? C5 C6 C7 C1 104.79(16) . . . . ? F1 C1 C7 C8 -141.31(15) . . . . ? C2 C1 C7 C8 8.8(2) . . . . ? C6 C1 C7 C8 112.61(17) . . . . ? F1 C1 C7 C6 106.08(14) . . . . ? C2 C1 C7 C6 -103.86(17) . . . . ? C6 C7 C8 C13 144.18(16) . . . . ? C1 C7 C8 C13 69.5(2) . . . . ? C6 C7 C8 C9 -38.3(2) . . . . ? C1 C7 C8 C9 -113.01(18) . . . . ? C9 C8 C13 C12 0.9(3) . . . . ? C7 C8 C13 C12 178.48(16) . . . . ? C8 C13 C12 C11 0.3(3) . . . . ? C13 C12 C11 C10 -1.3(3) . . . . ? C12 C11 C10 C9 1.1(3) . . . . ? C11 C10 C9 C8 0.2(3) . . . . ? C13 C8 C9 C10 -1.2(3) . . . . ? C7 C8 C9 C10 -178.68(17) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 30.48 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.344 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.050 #====================================================================== _eof