# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 loop_ _publ_author_name 'Kenji Uneyama' 'Hideki Amii' 'Mitsuhiro Kohda' 'Motoharu Seo' _publ_contact_author_name 'Kenji Uneyama' _publ_contact_author_address ; Department of Applied Chemistry, Faculty of Engineering Okayama University Tsushimanaka 3-1-1, Okayama Okayama 700-8530 JAPAN ; _publ_contact_author_email uneyamak@cc.okayama-u.ac.jp _publ_contact_author_fax ' (+81)-86-251-8021 ' _publ_contact_author_phone ' (+81)-86-251-8075 ' _publ_contact_letter ; ? ; _publ_requested_category ' CHOOSE FI FM FO CI CM CO or AD' _publ_requested_coeditor_name ? #------------------------------------------------------------------------------ # TITLE AND AUTHOR LIST _publ_section_title ; A novel route to the fluorinated diimines: carbon monoxide-promoted reductive homocoupling of fluorinated imidoyl iodides in the presence of a palladium catalyst ; _publ_section_abstract ; A new catalytic access to the fluorinated alpha-diimines which involves palladium(0)-catalyzed reductive dimerization of the imidoyl iodides is described. ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation, Rigaku Corporation. (2000). teXsan. Single Crystal Structure Analysis Software. Version 1.11. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Rigaku, 3-9-12 Akishima, Tokyo, Japan. Zachariasen, W. H. (1967). Acta Cryst. 23, 558-564. ; #------------------------------------------------------------------------------ data_p-Cl _database_code_CSD 206534 _audit_creation_date 'Fri May 2 22:02:46 2003' _audit_creation_method 'by teXsan' _audit_update_record ? #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C16 H8 Cl2 F6 N2 ' _chemical_formula_moiety 'C16 H8 Cl2 F6 N2 ' _chemical_formula_weight 413.15 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 2/n 1' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,-y,1/2+z -x,-y,-z 1/2-x,y,1/2-z _cell_length_a 7.2370(8) _cell_length_b 9.150(2) _cell_length_c 13.068(2) _cell_angle_alpha 90 _cell_angle_beta 100.907(9) _cell_angle_gamma 90 _cell_volume 849.7(2) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _cell_measurement_temperature 288.2 #------------------------------------------------------------------------------ _exptl_crystal_description unknown _exptl_crystal_colour yellow _exptl_crystal_size_max 0.000 _exptl_crystal_size_mid 0.000 _exptl_crystal_size_min 0.000 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.615 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.445 _exptl_absorpt_correction_type none #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K¥a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-IV Imaging Plate' _diffrn_measurement_method ¥w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 1430 _diffrn_reflns_av_R_equivalents ? _diffrn_reflns_theta_max 25.18 _diffrn_measured_fraction_theta_max 0.8943 _diffrn_reflns_theta_full 25.18 _diffrn_measured_fraction_theta_full 0.8943 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 5.0 sigma(F^2^). The weighted R-factor (wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F^2^ > 5.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 1371 _reflns_number_gt 1115 _reflns_threshold_expression F^2^>5.0¥s(F^2^) _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt 0.0702 _refine_ls_wR_factor_ref 0.1371 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1115 _refine_ls_number_parameters 119 _refine_ls_goodness_of_fit_ref 1.387 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[¥s^2^(Fo) + 0.01000|Fo|^2^]' _refine_ls_shift/su_max 0.0046 _refine_diff_density_max 0.26 _refine_diff_density_min -0.25 _refine_ls_extinction_method 'Zachariasen(1967) type 2 Gaussian isotropic' _refine_ls_extinction_coef 0.23(5) _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; F F 0.017 0.010 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Cl Cl 0.148 0.159 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 Cl(1) Cl 1.2103(2) 0.8440(2) 0.5954(1) 0.1049(6) Uani 1.00 d . . . F(1) F 0.5600(5) 0.0681(4) 0.6138(3) 0.123(1) Uani 1.00 d . . . F(2) F 0.5315(4) 0.0882(3) 0.7708(3) 0.109(1) Uani 1.00 d . . . F(3) F 0.3595(3) 0.2123(4) 0.6558(3) 0.104(1) Uani 1.00 d . . . N(2) N 0.6611(4) 0.3765(3) 0.6283(2) 0.0548(8) Uani 1.00 d . . . C(1) C 0.7349(5) 0.6322(5) 0.6076(3) 0.067(1) Uani 1.00 d . . . C(2) C 0.5304(5) 0.1612(4) 0.6842(3) 0.066(1) Uani 1.00 d . . . C(5) C 1.1124(5) 0.5670(5) 0.6276(3) 0.065(1) Uani 1.00 d . . . C(6) C 0.9862(5) 0.4568(4) 0.6370(3) 0.058(1) Uani 1.00 d . . . C(7) C 0.8638(6) 0.7408(5) 0.6004(4) 0.075(1) Uani 1.00 d . . . C(8) C 1.0489(6) 0.7076(5) 0.6090(3) 0.068(1) Uani 1.00 d . . . C(9) C 0.7978(4) 0.4884(4) 0.6275(2) 0.0530(9) Uani 1.00 d . . . C(10) C 0.6774(4) 0.2840(3) 0.6996(3) 0.0507(9) Uani 1.00 d . . . H(1) H 0.6047 0.6547 0.5992 0.0800 Uiso 1.00 calc . . . H(2) H 1.2425 0.5456 0.6339 0.0781 Uiso 1.00 calc . . . H(3) H 1.0294 0.3593 0.6500 0.0700 Uiso 1.00 calc . . . H(4) H 0.8230 0.8392 0.5893 0.0901 Uiso 1.00 calc . . . 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 Cl(1) 0.114(1) 0.089(1) 0.122(1) -0.0487(7) 0.0487(9) -0.0137(7) F(1) 0.121(2) 0.101(2) 0.168(3) -0.055(2) 0.079(2) -0.072(2) F(2) 0.113(2) 0.098(2) 0.115(2) -0.044(2) 0.014(2) 0.027(2) F(3) 0.050(2) 0.109(2) 0.149(3) -0.023(1) 0.010(1) 0.003(2) N(2) 0.043(2) 0.060(2) 0.061(2) -0.005(1) 0.009(1) -0.004(1) C(1) 0.053(2) 0.065(2) 0.084(3) 0.007(1) 0.018(2) 0.002(2) C(2) 0.058(2) 0.069(2) 0.074(2) -0.010(1) 0.020(2) -0.007(2) C(5) 0.054(2) 0.082(3) 0.061(2) -0.010(2) 0.016(1) -0.001(2) C(6) 0.058(2) 0.061(2) 0.056(2) -0.002(1) 0.010(1) 0.005(2) C(7) 0.081(3) 0.062(3) 0.088(3) 0.000(2) 0.032(2) 0.004(2) C(8) 0.077(3) 0.068(2) 0.061(2) -0.022(2) 0.019(2) -0.008(2) C(9) 0.049(2) 0.059(2) 0.050(2) -0.008(1) 0.006(1) 0.000(1) C(10) 0.043(2) 0.052(2) 0.059(2) -0.001(1) 0.015(1) -0.005(1) #------------------------------------------------------------------------------ _computing_data_collection PROCESS _computing_cell_refinement PROCESS _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _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 ? ? ? ? ? ? # -- ENTER BONDS HERE, ONE PER LINE -- # e.g. C1 C2 1.541(1) . . yes #------------------------------------------------------------------------------ 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 # -- ENTER ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 109.4(3) . . . yes ? ? ? ? ? ? ? ? #------------------------------------------------------------------------------ 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 # -- ENTER TORSION ANGLES HERE, ONE PER LINE -- # e.g. C1 C2 C3 C4 109.4(3) . . . . yes ? ? ? ? ? ? ? ? ? ? #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? # -- ENTER BONDS HERE, ONE PER LINE -- # e.g. O1 N1 1.541(1) . . yes #------------------------------------------------------------------------------ #------------------------------------------------------------------------------