# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1754 ######################################## # # # CIF generated by the Xtal System # # # ######################################## data_global _audit_creation_method Xtal3.7 _audit_creation_date 00-05-24 _audit_update_record ? #============================================================================== # (Publishing Staff Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # 1. SUBMISSION DETAILS #---------------------- _publ_contact_author_name ? #<< name in format "Smith, X. W." _publ_contact_author_address #<< address of contact author ; ? ; _publ_contact_author_email ? _publ_contact_author_fax ? _publ_contact_author_phone ? _publ_contact_letter #<< contact letter ; ? ; _publ_requested_journal ? #<< journal name e.g. "Section C" _publ_requested_category ? #<< paper category e.g. "FO" _publ_section_title #<< paper title text ; ? ; _publ_section_title_footnote #<< paper footnote text ; ? ; loop_ _publ_author_name _publ_author_footnote _publ_author_address #<< complete address as text ? #<< author name e.g. "Jones, X.W." ? #<< footnote otherwise leave as ? ; ? ; _publ_section_synopsis #<< synopsis if FI,CI,CM,CO papers ; ? ; _publ_section_abstract #<< abstract text ; ? ; _publ_section_comment #<< scientific commentary text ; ? ; _publ_section_acknowledgements #<< acknowledgements text ; ? ; _publ_section_references #<< references text ; ? ; _publ_section_figure_captions #<< figure captions ; ? ; #======================================================================= # Data block for single structure (one for each study in the paper) #======================================================================= data_MAT1 # 2. EXPERIMENTAL DATA #--------------------- _publ_section_exptl_prep #<< material & crystal preparation text ; ? ; _publ_section_exptl_refinement #<< crystallographic methods used ; ? ; _chemical_formula_sum 'C17 H17 F6 N1 O2 Pd1' _chemical_formula_moiety ? _chemical_formula_weight 487.74 _chemical_melting_point ? _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P_-1 _symmetry_space_group_name_Hall -p_1 loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,-z _cell_length_a 8.314(6) _cell_length_b 9.565(5) _cell_length_c 12.293(4) _cell_angle_alpha 77.57(7) _cell_angle_beta 87.72(4) _cell_angle_gamma 79.55(14) _cell_volume 938.8(10) _cell_formula_units_Z 2 _exptl_crystal_density_diffrn 1.725 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.0 _cell_measurement_theta_max 18.2 _cell_measurement_temperature 293 _exptl_absorpt_coefficient_mu 1.057 _exptl_crystal_description block _exptl_crystal_size_max .27 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .18 _exptl_crystal_size_rad ? _exptl_crystal_colour yellow _diffrn_measurement_device_type CAD4 _diffrn_measurement_method omega/2theta _diffrn_detector_area_resol_mean ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _diffrn_reflns_number 5916 _reflns_number_total 5559 _reflns_Friedel_coverage 0 _reflns_number_gt 4488 _reflns_threshold_expression 'F > 2.50 sig(F )' _diffrn_reflns_theta_max 30.26 _diffrn_reflns_theta_full ? _diffrn_measured_fraction_theta_max ? _diffrn_measured_fraction_theta_full ? _diffrn_reflns_av_R_equivalents .009 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 #<< do not append units _diffrn_standards_decay_% <1.0 #<< do not append % _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .037 _refine_ls_wR_factor_ref .037 _refine_ls_goodness_of_fit_ref 2.947 _refine_ls_number_reflns 5297 _refine_ls_number_parameters 295 _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 1/sigma _refine_ls_hydrogen_treatment riding _refine_ls_shift/su_max .592 _refine_diff_density_min -.893 _refine_diff_density_max .869 _refine_ls_extinction_method ? _refine_ls_extinction_coef .00000 _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? # 3. Information for the "methods" section #----------------------------------------- _computing_data_collection 'cad4 DATCOL' _computing_cell_refinement 'cad4 SETANG LS' _computing_data_reduction 'xtal DIFDAT ADDREF SORTRF' _computing_structure_solution 'xtal FOURR' _computing_structure_refinement 'xtal CRYLSQ' _computing_molecular_graphics 'xtal ORTEP' _computing_publication_material 'xtal BONDLA CIFIO' # 4. Supplementary data for validation and tables #------------------------------------------------ loop_ _atom_type_symbol _atom_type_description _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Pd ? 0 2 -1.177 1.007 'Int Tables Vol IV Tables 2.2B and 2.3.1' F ? 0 12 .014 .01 'Int Tables Vol IV Tables 2.2B and 2.3.1' C ? 0 34 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1' O ? 0 4 .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1' N ? 0 2 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1' H ? 0 34 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Pd .28233(3) .44957(2) .086119(18) .04770(15) Uani ? ? 1.00000 ? ? N1 .1151(3) .6291(2) .0633(2) .0533(18) Uani ? ? 1.00000 ? ? O1 .4434(2) .2629(2) .09304(17) .0574(15) Uani ? ? 1.00000 ? ? O2 .2705(3) .4055(2) .26172(17) .0636(17) Uani ? ? 1.00000 ? ? C1 .2768(3) .4969(3) -.0760(2) .050(2) Uani ? ? 1.00000 ? ? C2 .1643(3) .6191(3) -.1206(3) .054(2) Uani ? ? 1.00000 ? ? C3 .1435(5) .6625(4) -.2350(3) .069(3) Uani ? ? 1.00000 ? ? C4 .2369(5) .5845(5) -.3041(3) .079(3) Uani ? ? 1.00000 ? ? C5 .3469(5) .4632(4) -.2602(3) .072(3) Uani ? ? 1.00000 ? ? C6 .3684(4) .4201(3) -.1472(3) .060(2) Uani ? ? 1.00000 ? ? C7 .0751(3) .6910(3) -.0374(3) .056(2) Uani ? ? 1.00000 ? ? C71 -.0469(5) .8257(4) -.0710(4) .077(3) Uani ? ? 1.00000 ? ? C11 .4888(3) .1758(3) .1810(3) .057(2) Uani ? ? 1.00000 ? ? C111 .5982(5) .0393(4) .1611(4) .082(3) Uani ? ? 1.00000 ? ? C12 .4505(4) .1827(4) .2899(3) .069(3) Uani ? ? 1.00000 ? ? C13 .3457(4) .2955(4) .3213(3) .064(3) Uani ? ? 1.00000 ? ? C131 .3148(8) .2843(6) .4439(3) .107(5) Uani ? ? 1.00000 ? ? C100 .0427(4) .6807(4) .1614(3) .062(3) Uani ? ? 1.00000 ? ? C200 .1556(4) .7571(4) .2104(3) .062(2) Uani ? ? 1.00000 ? ? C300 .0924(5) .7879(5) .3216(4) .083(4) Uani ? ? 1.00000 ? ? C400 .1957(9) .8663(7) .3723(5) .125(6) Uani ? ? 1.00000 ? ? F1 .6899(3) .0627(3) .0747(3) .127(3) Uani ? ? 1.00000 ? ? F2 .5142(4) -.0515(3) .1448(3) .161(4) Uani ? ? 1.00000 ? ? F3 .6962(5) -.0219(4) .2409(3) .212(4) Uani ? ? 1.00000 ? ? F4 .3843(6) .1771(5) .5091(2) .228(5) Uani ? ? 1.00000 ? ? F5 .3574(9) .3846(5) .4773(3) .258(7) Uani ? ? 1.00000 ? ? F6 .1708(5) .2958(9) .4672(3) .282(7) Uani ? ? 1.00000 ? ? H31 .064(4) .733(3) -.261(3) .07000 Uiso ? ? 1.00000 ? ? H41 .227(4) .608(3) -.374(3) .07000 Uiso ? ? 1.00000 ? ? H51 .423(4) .415(3) -.307(3) .07000 Uiso ? ? 1.00000 ? ? H61 .440(4) .340(3) -.118(3) .07000 Uiso ? ? 1.00000 ? ? H711 -.050(5) .865(4) -.018(3) .08000 Uiso ? ? 1.00000 ? ? H712 -.147(4) .800(4) -.039(3) .08000 Uiso ? ? 1.00000 ? ? H713 -.085(4) .850(4) -.144(3) .08000 Uiso ? ? 1.00000 ? ? H121 .484(4) .116(3) .338(3) .07000 Uiso ? ? 1.00000 ? ? H101 .026(4) .603(3) .215(3) .07000 Uiso ? ? 1.00000 ? ? H102 -.064(4) .739(3) .136(2) .07000 Uiso ? ? 1.00000 ? ? H201 .266(4) .698(3) .221(2) .07000 Uiso ? ? 1.00000 ? ? H202 .178(4) .844(3) .154(2) .07000 Uiso ? ? 1.00000 ? ? H301 -.012(4) .858(4) .303(3) .08000 Uiso ? ? 1.00000 ? ? H302 .093(4) .703(4) .382(3) .08000 Uiso ? ? 1.00000 ? ? H401 .163(5) .889(5) .439(4) .12000 Uiso ? ? 1.00000 ? ? H402 .210(5) .965(5) .315(3) .12000 Uiso ? ? 1.00000 ? ? H403 .299(5) .795(5) .398(4) .12000 Uiso ? ? 1.00000 ? ? 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 Pd .04641(12) .04390(11) .05256(12) -.00184(8) .00160(8) -.01518(9) N1 .0474(13) .0456(12) .0698(16) -.0051(10) .0059(11) -.0219(12) O1 .0549(12) .0503(11) .0637(12) .0024(9) .0008(10) -.0151(10) O2 .0682(13) .0623(13) .0569(12) -.0005(11) .0030(10) -.0155(10) C1 .0479(15) .0490(15) .0564(16) -.0111(12) .0012(12) -.0147(13) C2 .0543(16) .0451(15) .0644(18) -.0118(13) -.0036(14) -.0117(13) C3 .080(2) .061(2) .064(2) -.0117(17) -.0167(18) -.0028(17) C4 .100(3) .086(3) .0523(19) -.025(2) -.001(2) -.012(2) C5 .079(2) .084(3) .059(2) -.021(2) .0118(18) -.0229(18) C6 .0585(19) .0610(19) .064(2) -.0082(14) .0088(15) -.0221(16) C7 .0493(16) .0412(14) .076(2) -.0089(12) -.0062(14) -.0113(14) C71 .065(2) .057(2) .103(3) .0070(16) -.015(2) -.021(2) C11 .0461(15) .0503(16) .075(2) -.0043(12) -.0076(14) -.0129(15) C111 .076(2) .062(2) .098(3) .0144(19) -.002(2) -.018(2) C12 .073(2) .064(2) .062(2) -.0015(17) -.0088(17) -.0042(16) C13 .066(2) .073(2) .0554(18) -.0171(17) -.0012(15) -.0133(16) C131 .134(4) .124(4) .053(2) .007(3) .009(3) -.022(3) C100 .0488(17) .0606(19) .080(2) -.0043(14) .0110(15) -.0274(16) C200 .0595(18) .0583(18) .069(2) -.0057(15) .0050(16) -.0223(16) C300 .084(3) .087(3) .082(3) -.002(2) .005(2) -.035(2) C400 .168(6) .135(5) .092(4) -.046(4) -.003(4) -.050(4) F1 .110(2) .0858(16) .170(3) .0171(14) .056(2) -.0333(17) F2 .139(3) .0706(16) .292(4) -.0263(17) .054(3) -.083(2) F3 .229(4) .196(3) .146(3) .159(3) -.071(3) -.048(2) F4 .359(6) .196(4) .0586(16) .095(4) -.006(3) .009(2) F5 .518(11) .206(4) .079(2) -.089(5) .022(4) -.077(3) F6 .128(3) .592(11) .076(2) -.021(5) .044(2) -.009(4) # 5. Molecular Geometry #---------------------- loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag #<< enter y(es) for value to be published Pd N1 . . 1.979(2) ? Pd O1 . . 2.017(2) ? Pd O2 . . 2.110(2) ? Pd C1 . . 1.947(3) ? N1 C7 . . 1.281(4) ? N1 C100 . . 1.467(5) ? O1 C11 . . 1.240(3) ? O2 C13 . . 1.225(4) ? C1 C2 . . 1.382(4) ? C1 C6 . . 1.381(4) ? C2 C3 . . 1.386(5) ? C2 C7 . . 1.458(4) ? C3 C4 . . 1.375(6) ? C3 H31 . . .87(3) ? C4 C5 . . 1.364(5) ? C4 H41 . . .85(3) ? C5 C6 . . 1.370(5) ? C5 H51 . . .96(3) ? C6 H61 . . .89(3) ? C7 C71 . . 1.480(4) ? C71 H711 . . .82(4) ? C71 H712 . . .95(3) ? C71 H713 . . .93(3) ? C11 C111 . . 1.510(5) ? C11 C12 . . 1.375(5) ? C111 F1 . . 1.286(5) ? C111 F2 . . 1.260(6) ? C111 F3 . . 1.270(5) ? C12 C13 . . 1.373(5) ? C12 H121 . . .79(3) ? C13 C131 . . 1.503(5) ? C131 F4 . . 1.223(6) ? C131 F5 . . 1.232(9) ? C131 F6 . . 1.211(7) ? C100 C200 . . 1.504(5) ? C100 H101 . . .91(3) ? C100 H102 . . .98(3) ? C200 C300 . . 1.514(6) ? C200 H201 . . .98(3) ? C200 H202 . . 1.00(3) ? C300 C400 . . 1.472(9) ? C300 H301 . . 1.00(3) ? C300 H302 . . .97(3) ? C400 H401 . . .91(5) ? C400 H402 . . 1.07(4) ? C400 H403 . . 1.01(4) ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag #<< enter yes for value to be published N1 Pd O1 . . . 173.45(10) ? N1 Pd O2 . . . 95.66(10) ? N1 Pd C1 . . . 80.75(12) ? O1 Pd O2 . . . 89.85(9) ? O1 Pd C1 . . . 93.61(11) ? O2 Pd C1 . . . 175.88(9) ? Pd N1 C7 . . . 117.0(2) ? Pd N1 C100 . . . 118.60(18) ? C7 N1 C100 . . . 124.3(2) ? Pd O1 C11 . . . 123.7(2) ? Pd O2 C13 . . . 123.6(2) ? Pd C1 C2 . . . 114.1(2) ? Pd C1 C6 . . . 127.0(2) ? C2 C1 C6 . . . 118.9(3) ? C1 C2 C3 . . . 120.2(3) ? C1 C2 C7 . . . 113.9(3) ? C3 C2 C7 . . . 125.8(3) ? C2 C3 C4 . . . 119.7(3) ? C2 C3 H31 . . . 119(2) ? C4 C3 H31 . . . 121(2) ? C3 C4 C5 . . . 120.1(3) ? C3 C4 H41 . . . 122(2) ? C5 C4 H41 . . . 118(2) ? C4 C5 C6 . . . 120.4(4) ? C4 C5 H51 . . . 121.0(16) ? C6 C5 H51 . . . 117.9(17) ? C1 C6 C5 . . . 120.6(3) ? C1 C6 H61 . . . 119(2) ? C5 C6 H61 . . . 120(2) ? N1 C7 C2 . . . 114.1(2) ? N1 C7 C71 . . . 124.9(3) ? C2 C7 C71 . . . 121.0(3) ? C7 C71 H711 . . . 104(2) ? C7 C71 H712 . . . 104.1(19) ? C7 C71 H713 . . . 118(2) ? H711 C71 H712 . . . 82(4) ? H711 C71 H713 . . . 138(3) ? H712 C71 H713 . . . 95(3) ? O1 C11 C111 . . . 112.4(3) ? O1 C11 C12 . . . 130.5(3) ? C111 C11 C12 . . . 117.1(3) ? C11 C111 F1 . . . 113.0(3) ? C11 C111 F2 . . . 110.7(3) ? C11 C111 F3 . . . 113.2(4) ? F1 C111 F2 . . . 106.1(4) ? F1 C111 F3 . . . 105.0(4) ? F2 C111 F3 . . . 108.4(4) ? C11 C12 C13 . . . 124.1(3) ? C11 C12 H121 . . . 119(2) ? C13 C12 H121 . . . 116(2) ? O2 C13 C12 . . . 128.3(3) ? O2 C13 C131 . . . 114.5(3) ? C12 C13 C131 . . . 117.2(3) ? C13 C131 F4 . . . 118.6(5) ? C13 C131 F5 . . . 111.9(5) ? C13 C131 F6 . . . 112.6(4) ? F4 C131 F5 . . . 102.3(5) ? F4 C131 F6 . . . 106.3(5) ? F5 C131 F6 . . . 103.5(6) ? N1 C100 C200 . . . 111.6(3) ? N1 C100 H101 . . . 109(2) ? N1 C100 H102 . . . 104.8(19) ? C200 C100 H101 . . . 107(2) ? C200 C100 H102 . . . 116(2) ? H101 C100 H102 . . . 108(3) ? C100 C200 C300 . . . 111.0(3) ? C100 C200 H201 . . . 111(2) ? C100 C200 H202 . . . 110(2) ? C300 C200 H201 . . . 109.1(18) ? C300 C200 H202 . . . 115(2) ? H201 C200 H202 . . . 101(2) ? C200 C300 C400 . . . 113.5(4) ? C200 C300 H301 . . . 104(2) ? C200 C300 H302 . . . 116(2) ? C400 C300 H301 . . . 105(2) ? C400 C300 H302 . . . 99(2) ? H301 C300 H302 . . . 119(3) ? C300 C400 H401 . . . 117(3) ? C300 C400 H402 . . . 110(3) ? C300 C400 H403 . . . 107(3) ? H401 C400 H402 . . . 108(4) ? H401 C400 H403 . . . 98(4) ? H402 C400 H403 . . . 117(3) ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag #<< enter yes for value to be published ? ? ? ? ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag #<< enter yes for value to be published ? ? ? ? ? ? ? ? ? ? ? #-------------------------------------------------------------------------- # Special items requested by author for inclusion in paper #-------------------------------------------------------------------------- loop_ _publ_manuscript_incl_extra_item _publ_manuscript_incl_extra_defn ? ? #-------------------------------------------------------------------------- # Items which are non-mandatory for Acta C submissions #-------------------------------------------------------------------------- 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 ? ? ? ? ? ? _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens ? _geom_special_details ? _cell_special_details ; ? ; _exptl_special_details ; ? ; _diffrn_special_details ; ? ; _chemical_compound_source ? _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_analytical ? _chemical_formula_structural ? _exptl_crystal_F_000 484 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? loop_ _diffrn_attenuator_code _diffrn_attenuator_scale ? ? _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _reflns_number_observed ? _reflns_d_resolution_high .705 _reflns_d_resolution_low 11.976 _diffrn_reflns_av_sigmaI/netI .016 _diffrn_reflns_theta_min 1.7 _diffrn_reflns_reduction_process 'No monochr Lp applied' _diffrn_ambient_temperature 293 _diffrn_radiation_source ? _diffrn_radiation_monochromator ? _diffrn_radiation_detector ? _refine_ls_extinction_expression ? _refine_ls_matrix_type full _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all .059 _refine_ls_wR_factor_all .037 _refine_ls_goodness_of_fit_all 2.651 _refine_ls_shift/su_mean .04 #========================================================================== # Structure Factor lists should be submitted as separate files #========================================================================== #data_ # but for xtal use the refln data is needed in same block loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_meas _refln_F_calc _refln_F_sigma _refln_F_squared_meas _refln_F_squared_calc _refln_F_squared_sigma _refln_observed_status _refln_F_meas_friedel _refln_F_sigma_friedel _refln_F_squared_meas_friedel _refln_F_squared_sigma_friedel ? ? ? ? ? ? ? ? ? ? ? ? ? ? #-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end-end