Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #============================================================================== # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Dr. Hans-Georg Stammler ; _publ_contact_author_phone '49 521 1066165' _publ_contact_author_fax '49 521 1066146' _publ_contact_author_email georg.stammler@uni-bielefeld.de _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for deposition To: DALTON@RSC.ORG Subject: Depositing Crystal Structure Data Dear Madam or Sir, please find enclosed the crystallographic data of compound3 'C23 H42 Cl F4 N P2 Pd' for deposition in your data file. With kind regards Beate Neumann ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office 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_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Reactivity of a palladium fluoro complex: catalytic activity based on carbon-fluorine activation reactions of pentafluoropyridine ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address T.Braun ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; J.Izundu ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; A.Steffen ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; B.Neumann ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; A.Stammler ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; H.-G.Stammler ; Fakult\"at f. Chemie Universit\"at Bielefeld 33615 Bielefeld Germany ; _publ_contact_author_name 'Dr. Hans-Georg Stammler' #========================================================================= data_compound3 _database_code_depnum_ccdc_archive 'CCDC 611054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H42 Cl F4 N P2 Pd' _chemical_formula_sum 'C23 H42 Cl F4 N P2 Pd' _chemical_formula_weight 612.37 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' Cl Cl 0.1484 0.1585 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd -0.9988 1.0072 '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/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 17.5230(2) _cell_length_b 12.2760(2) _cell_length_c 13.0610(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.2260(8) _cell_angle_gamma 90.00 _cell_volume 2735.06(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8331 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description irregular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8501 _exptl_absorpt_correction_T_max 0.9125 _exptl_absorpt_process_details 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _exptl_special_details ; ; _diffrn_ambient_temperature 100(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 62968 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0391 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7963 _reflns_number_gt 6428 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KappaCCD ' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'SHELXL-97 ' _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^)+(0.0323P)^2^+0.3610P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7963 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0283 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 Pd1 Pd 0.223275(7) -0.009412(10) 0.252126(10) 0.01495(4) Uani 1 1 d . . . Cl1 Cl 0.14676(2) -0.16540(3) 0.19346(4) 0.02301(10) Uani 1 1 d . . . P1 P 0.31798(2) -0.07459(4) 0.16367(3) 0.01730(9) Uani 1 1 d . . . P2 P 0.12345(2) 0.05257(3) 0.33343(3) 0.01520(9) Uani 1 1 d . . . F1 F 0.24303(6) 0.22939(8) 0.15160(8) 0.0267(2) Uani 1 1 d . . . F2 F 0.33890(7) 0.39257(9) 0.22930(11) 0.0386(3) Uani 1 1 d . . . F3 F 0.44366(7) 0.20793(10) 0.52643(10) 0.0429(3) Uani 1 1 d . . . F4 F 0.35313(6) 0.03396(9) 0.46531(9) 0.0278(2) Uani 1 1 d . . . N1 N 0.39144(9) 0.29971(13) 0.37774(14) 0.0307(4) Uani 1 1 d . . . C1 C 0.33315(10) -0.22317(14) 0.18481(15) 0.0219(4) Uani 1 1 d . . . H1 H 0.2816 -0.2571 0.1515 0.026 Uiso 1 1 calc R . . C2 C 0.34933(12) -0.25703(16) 0.30066(16) 0.0310(4) Uani 1 1 d . . . H2A H 0.3419 -0.3358 0.3054 0.046 Uiso 1 1 calc R . . H2B H 0.3131 -0.2188 0.3353 0.046 Uiso 1 1 calc R . . H2C H 0.4034 -0.2381 0.3354 0.046 Uiso 1 1 calc R . . C3 C 0.39221(11) -0.27493(16) 0.12855(17) 0.0320(5) Uani 1 1 d . . . H3A H 0.4454 -0.2525 0.1636 0.048 Uiso 1 1 calc R . . H3B H 0.3807 -0.2508 0.0551 0.048 Uiso 1 1 calc R . . H3C H 0.3881 -0.3545 0.1311 0.048 Uiso 1 1 calc R . . C4 C 0.28509(10) -0.06171(15) 0.01888(14) 0.0233(4) Uani 1 1 d . . . H4 H 0.3313 -0.0786 -0.0114 0.028 Uiso 1 1 calc R . . C5 C 0.21960(11) -0.13937(18) -0.03194(16) 0.0317(4) Uani 1 1 d . . . H5A H 0.1729 -0.1244 -0.0048 0.048 Uiso 1 1 calc R . . H5B H 0.2366 -0.2147 -0.0154 0.048 Uiso 1 1 calc R . . H5C H 0.2071 -0.1290 -0.1084 0.048 Uiso 1 1 calc R . . C6 C 0.26091(12) 0.05586(18) -0.01143(16) 0.0336(5) Uani 1 1 d . . . H6A H 0.2519 0.0643 -0.0879 0.050 Uiso 1 1 calc R . . H6B H 0.3027 0.1055 0.0231 0.050 Uiso 1 1 calc R . . H6C H 0.2126 0.0731 0.0111 0.050 Uiso 1 1 calc R . . C7 C 0.41422(10) -0.00206(15) 0.19449(16) 0.0245(4) Uani 1 1 d . . . H7 H 0.4018 0.0761 0.2047 0.029 Uiso 1 1 calc R . . C8 C 0.46114(11) -0.00276(16) 0.10920(18) 0.0312(5) Uani 1 1 d . . . H8A H 0.5099 0.0382 0.1337 0.047 Uiso 1 1 calc R . . H8B H 0.4301 0.0312 0.0452 0.047 Uiso 1 1 calc R . . H8C H 0.4735 -0.0781 0.0940 0.047 Uiso 1 1 calc R . . C9 C 0.46525(10) -0.04006(18) 0.29957(17) 0.0303(4) Uani 1 1 d . . . H9A H 0.4875 -0.1117 0.2906 0.046 Uiso 1 1 calc R . . H9B H 0.4332 -0.0451 0.3518 0.046 Uiso 1 1 calc R . . H9C H 0.5078 0.0123 0.3236 0.046 Uiso 1 1 calc R . . C10 C 0.13224(10) 0.19729(13) 0.37743(14) 0.0195(3) Uani 1 1 d . . . H10 H 0.1891 0.2102 0.4088 0.023 Uiso 1 1 calc R . . C11 C 0.10950(11) 0.27495(14) 0.28375(16) 0.0263(4) Uani 1 1 d . . . H11A H 0.0523 0.2780 0.2604 0.039 Uiso 1 1 calc R . . H11B H 0.1318 0.2487 0.2260 0.039 Uiso 1 1 calc R . . H11C H 0.1299 0.3479 0.3048 0.039 Uiso 1 1 calc R . . C12 C 0.08820(11) 0.22977(16) 0.46193(16) 0.0275(4) Uani 1 1 d . . . H12A H 0.0993 0.3062 0.4815 0.041 Uiso 1 1 calc R . . H12B H 0.1055 0.1835 0.5241 0.041 Uiso 1 1 calc R . . H12C H 0.0317 0.2203 0.4341 0.041 Uiso 1 1 calc R . . C13 C 0.11809(10) -0.02295(14) 0.45438(14) 0.0206(4) Uani 1 1 d . . . H13 H 0.0802 0.0168 0.4876 0.025 Uiso 1 1 calc R . . C14 C 0.08759(10) -0.13941(15) 0.43356(15) 0.0254(4) Uani 1 1 d . . . H14A H 0.1177 -0.1772 0.3897 0.038 Uiso 1 1 calc R . . H14B H 0.0321 -0.1376 0.3971 0.038 Uiso 1 1 calc R . . H14C H 0.0934 -0.1780 0.5006 0.038 Uiso 1 1 calc R . . C15 C 0.19788(11) -0.02158(17) 0.53362(16) 0.0283(4) Uani 1 1 d . . . H15A H 0.1920 -0.0520 0.6008 0.042 Uiso 1 1 calc R . . H15B H 0.2169 0.0536 0.5443 0.042 Uiso 1 1 calc R . . H15C H 0.2355 -0.0654 0.5063 0.042 Uiso 1 1 calc R . . C16 C 0.02617(9) 0.02939(14) 0.24462(13) 0.0168(3) Uani 1 1 d . . . H16 H 0.0206 -0.0516 0.2387 0.020 Uiso 1 1 calc R . . C17 C 0.02030(10) 0.06944(15) 0.13214(14) 0.0228(4) Uani 1 1 d . . . H17A H -0.0271 0.0395 0.0858 0.034 Uiso 1 1 calc R . . H17B H 0.0665 0.0452 0.1079 0.034 Uiso 1 1 calc R . . H17C H 0.0178 0.1492 0.1306 0.034 Uiso 1 1 calc R . . C18 C -0.04418(9) 0.06771(15) 0.28673(14) 0.0213(4) Uani 1 1 d . . . H18A H -0.0460 0.1475 0.2864 0.032 Uiso 1 1 calc R . . H18B H -0.0388 0.0411 0.3588 0.032 Uiso 1 1 calc R . . H18C H -0.0926 0.0390 0.2419 0.032 Uiso 1 1 calc R . . C19 C 0.29098(9) 0.12047(13) 0.30460(14) 0.0182(3) Uani 1 1 d . . . C20 C 0.29114(9) 0.21639(14) 0.24809(14) 0.0207(4) Uani 1 1 d . . . C21 C 0.34079(10) 0.30111(15) 0.28662(16) 0.0263(4) Uani 1 1 d . . . C22 C 0.39226(10) 0.21023(16) 0.43287(16) 0.0280(4) Uani 1 1 d . . . C23 C 0.34447(10) 0.12144(14) 0.40073(15) 0.0229(4) Uani 1 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 Pd1 0.01475(7) 0.01477(7) 0.01595(7) -0.00087(5) 0.00478(5) -0.00062(4) Cl1 0.0218(2) 0.0185(2) 0.0310(2) -0.00690(17) 0.01058(18) -0.00389(15) P1 0.01591(19) 0.0188(2) 0.0181(2) 0.00093(17) 0.00564(17) 0.00154(16) P2 0.01555(19) 0.0158(2) 0.0146(2) -0.00047(16) 0.00423(16) 0.00005(16) F1 0.0286(5) 0.0248(5) 0.0251(6) 0.0038(5) 0.0025(5) -0.0017(4) F2 0.0377(6) 0.0209(6) 0.0552(8) 0.0088(5) 0.0063(6) -0.0078(5) F3 0.0357(7) 0.0463(7) 0.0369(7) -0.0057(6) -0.0121(6) -0.0092(6) F4 0.0262(5) 0.0306(6) 0.0246(6) 0.0052(5) 0.0018(5) -0.0010(5) N1 0.0243(8) 0.0235(8) 0.0426(11) -0.0056(7) 0.0040(8) -0.0050(6) C1 0.0204(8) 0.0182(8) 0.0278(10) -0.0008(7) 0.0070(7) 0.0025(7) C2 0.0332(10) 0.0279(10) 0.0330(11) 0.0092(9) 0.0099(9) 0.0044(8) C3 0.0295(10) 0.0279(10) 0.0405(12) -0.0032(9) 0.0120(9) 0.0098(8) C4 0.0234(9) 0.0299(10) 0.0178(9) 0.0025(8) 0.0075(7) 0.0062(7) C5 0.0276(10) 0.0444(12) 0.0219(10) -0.0044(9) 0.0033(8) 0.0019(9) C6 0.0381(11) 0.0386(12) 0.0251(11) 0.0115(9) 0.0094(9) 0.0125(9) C7 0.0178(8) 0.0264(10) 0.0308(11) 0.0020(8) 0.0092(8) -0.0008(7) C8 0.0222(9) 0.0341(11) 0.0412(13) 0.0050(9) 0.0153(9) 0.0030(8) C9 0.0190(9) 0.0370(11) 0.0333(11) -0.0002(9) 0.0025(8) -0.0024(8) C10 0.0191(8) 0.0180(8) 0.0217(9) -0.0056(7) 0.0051(7) -0.0013(6) C11 0.0288(9) 0.0172(9) 0.0322(11) -0.0011(8) 0.0055(8) 0.0011(7) C12 0.0262(9) 0.0278(10) 0.0305(11) -0.0118(8) 0.0103(8) -0.0023(7) C13 0.0198(8) 0.0258(9) 0.0170(9) 0.0023(7) 0.0058(7) -0.0007(7) C14 0.0258(9) 0.0251(9) 0.0257(10) 0.0068(8) 0.0067(8) -0.0007(7) C15 0.0255(9) 0.0380(11) 0.0193(10) 0.0078(8) 0.0007(8) -0.0017(8) C16 0.0167(7) 0.0176(8) 0.0162(8) -0.0016(6) 0.0040(6) -0.0011(6) C17 0.0242(9) 0.0252(9) 0.0176(9) -0.0014(7) 0.0019(7) 0.0002(7) C18 0.0170(8) 0.0252(9) 0.0220(9) -0.0011(7) 0.0051(7) 0.0017(7) C19 0.0154(7) 0.0197(8) 0.0211(9) -0.0018(7) 0.0076(7) 0.0001(6) C20 0.0172(8) 0.0215(9) 0.0236(10) -0.0022(7) 0.0051(7) 0.0009(6) C21 0.0227(9) 0.0190(9) 0.0373(12) 0.0000(8) 0.0071(8) -0.0018(7) C22 0.0202(8) 0.0305(10) 0.0303(11) -0.0075(8) -0.0006(8) -0.0027(7) C23 0.0209(8) 0.0233(9) 0.0256(10) -0.0004(7) 0.0075(7) -0.0002(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 Pd1 C19 2.0118(17) . ? Pd1 Cl1 2.3625(4) . ? Pd1 P1 2.3678(4) . ? Pd1 P2 2.3699(4) . ? P1 C4 1.8533(18) . ? P1 C1 1.8547(18) . ? P1 C7 1.8677(18) . ? P2 C16 1.8514(17) . ? P2 C13 1.8525(18) . ? P2 C10 1.8627(17) . ? F1 C20 1.356(2) . ? F2 C21 1.346(2) . ? F3 C22 1.342(2) . ? F4 C23 1.353(2) . ? N1 C22 1.312(3) . ? N1 C21 1.312(3) . ? C1 C2 1.532(3) . ? C1 C3 1.537(2) . ? C4 C5 1.522(3) . ? C4 C6 1.531(3) . ? C7 C8 1.528(3) . ? C7 C9 1.529(3) . ? C10 C11 1.530(3) . ? C10 C12 1.537(2) . ? C13 C14 1.529(3) . ? C13 C15 1.538(3) . ? C16 C17 1.530(2) . ? C16 C18 1.534(2) . ? C19 C23 1.384(3) . ? C19 C20 1.390(2) . ? C20 C21 1.375(2) . ? C22 C23 1.380(3) . ? 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 C19 Pd1 Cl1 178.26(5) . . ? C19 Pd1 P1 90.55(5) . . ? Cl1 Pd1 P1 88.679(15) . . ? C19 Pd1 P2 91.78(4) . . ? Cl1 Pd1 P2 89.041(14) . . ? P1 Pd1 P2 177.089(16) . . ? C4 P1 C1 103.67(8) . . ? C4 P1 C7 103.53(9) . . ? C1 P1 C7 110.19(8) . . ? C4 P1 Pd1 112.33(6) . . ? C1 P1 Pd1 110.62(6) . . ? C7 P1 Pd1 115.65(6) . . ? C16 P2 C13 103.78(8) . . ? C16 P2 C10 109.83(8) . . ? C13 P2 C10 103.35(8) . . ? C16 P2 Pd1 109.77(5) . . ? C13 P2 Pd1 114.09(6) . . ? C10 P2 Pd1 115.28(5) . . ? C22 N1 C21 115.42(16) . . ? C2 C1 C3 111.55(15) . . ? C2 C1 P1 113.69(13) . . ? C3 C1 P1 115.12(13) . . ? C5 C4 C6 109.95(16) . . ? C5 C4 P1 114.76(13) . . ? C6 C4 P1 110.33(13) . . ? C8 C7 C9 110.54(15) . . ? C8 C7 P1 116.74(14) . . ? C9 C7 P1 111.20(13) . . ? C11 C10 C12 109.32(15) . . ? C11 C10 P2 111.06(12) . . ? C12 C10 P2 116.70(12) . . ? C14 C13 C15 110.92(15) . . ? C14 C13 P2 113.59(13) . . ? C15 C13 P2 110.66(12) . . ? C17 C16 C18 111.27(14) . . ? C17 C16 P2 113.71(11) . . ? C18 C16 P2 115.37(12) . . ? C23 C19 C20 113.02(15) . . ? C23 C19 Pd1 122.68(13) . . ? C20 C19 Pd1 124.27(13) . . ? F1 C20 C21 117.25(16) . . ? F1 C20 C19 121.13(15) . . ? C21 C20 C19 121.61(17) . . ? N1 C21 F2 116.17(16) . . ? N1 C21 C20 124.20(18) . . ? F2 C21 C20 119.63(18) . . ? N1 C22 F3 115.99(16) . . ? N1 C22 C23 124.38(18) . . ? F3 C22 C23 119.62(18) . . ? F4 C23 C22 117.63(17) . . ? F4 C23 C19 120.99(15) . . ? C22 C23 C19 121.36(17) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.784 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.080